2-(3-alkylthiobenzoyl)cyclohexanediones and their use as herbicides

ABSTRACT

2-(3-Alkylthiobenzoyl)cyclohexanediones of the formula (I) are described as herbicides. 
     
       
         
         
             
             
         
       
     
     In this formula (I), X, Y, R 1  to R 8  represent radicals such as hydrogen, organic radicals such as alkyl and alkoxy.

CROSS REFERENCE TO RELATED APPLICATION

This application claims priority to EP 09009777.5 filed Jul. 29, 2009,and U.S. Provisional Application Ser. No. 61/229,365 filed Jul. 29,2009, the entire contents of which are incorporated by reference intheir entireties.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The invention relates to the technical field of herbicides, inparticular that of herbicides for the selective control of broad-leavedweeds and weed grasses in crops of useful plants.

2. Description of Related Art

It is already known from various publications that certainbenzoylcyclohexanediones have herbicidal properties. Thus, U.S. Pat. No.4,780,127, EP-A-338 992, EP-A-249 150 and EP-A-137963 describebenzoylcyclohexanediones substituted at the phenyl ring by variousradicals.

The herbicidal activity of the compounds known from these publications,however, is frequently inadequate. It is therefore an object of thepresent invention to provide further herbicidally active compoundshaving properties which—relative to those of the compounds disclosed inthe state of the art—are improved.

SUMMARY

It has now been found that benzoylcyclohexanediones whose phenyl ring issubstituted in the 2-, 3- and 4-position by selected radicals areparticularly suitable as herbicides.

The present invention provides 2-(3-alkylthiobenzoyl)cyclohexanedionesof the formula (I) or salts thereof

in whichR¹ is (C₁-C₆)-alkyl,R² is hydroxyl, SR¹³, NR¹⁴R¹⁵,R³ and R⁸ independently of one another are hydrogen or (C₁-C₄)-alkyl, orthe radicals R³ and R⁸ together form the unit Z which represents anoxygen or sulfur atom or one to four methylene groups,R⁴ and R⁷ independently of one another are hydrogen or (C₁-C₄)-alkyl,R⁵ and R⁶ independently of one another are hydrogen or (C₁-C₄)-alkyl ortogether with the carbon atom to which they are attached form a carbonylgroup,

X is OR⁹, OCOR⁹, OSO₂R¹⁰,

R⁹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals from the group consisting of halogen, OR¹¹ andS(O)_(m)R¹²,R¹⁰ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals from the group consisting of halogen, OR¹¹ andS(O)_(m)R¹²,R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,R¹² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,R¹³ is (C₁-C₄)-alkyl, phenyl which is substituted by s radicals from thegroup consisting of nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxy or is partially or fullyhalogenated phenyl,R¹⁴ is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy,R¹⁵ is hydrogen or (C₁-C₄)-alkyl,orR¹⁴ and R¹⁵ together with the nitrogen atom to which they are attachedform a 5- or 6-membered saturated, partially saturated or unsaturatedring,which contains zero, one or two heteroatoms selected from the groupconsisting of oxygen, sulfur and nitrogen,which is substituted by s radicals from the group consisting of cyano,halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and(C₁-C₄)-haloalkoxy,Y is (C₁-C₆)-haloalkyl,m is 0, 1 or 2,n is 0, 1 or 2,s is 0, 1, 2 or 3.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In formula (I) and all the formulae below, alkyl radicals having morethan two carbon atoms can be straight-chain or branched. Alkyl radicalsare, for example, methyl, ethyl, n-oder isopropyl, n-, iso-, t-oder2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and1,3-dimethylbutyl. Halogen represents fluorine, chlorine, bromine oriodine.

Where a group is substituted by a plurality of radicals, this means thatthis group is substituted by one or more identical or differentrepresentatives of the radicals mentioned.

Depending on the nature and the attachment of the substituents, thecompounds of the formula (I) may be present as stereoisomers. If, forexample, one or more asymmetrically substituted carbon atoms arepresent, there may be enantiomers and diastereomers. There may also bestereoisomers if n is 1 (sulfoxides). Stereoisomers may be obtained fromthe mixtures resulting from the preparation using customary separationmethods, for example by chromatographic separation techniques. It isalso possible to prepare stereoisomers selectively by usingstereoselective reactions employing optically active starting materialsand/or auxiliaries. The invention also relates to all stereoisomers andmixtures thereof embraced by the formula (I) but not specificallydefined.

Preferred are compounds of the formula (I) in which

R¹ is methyl, ethyl, n-propyl or isopropyl,R² is hydroxyl,R³ and R⁸ independently of one another are hydrogen or (C₁-C₄)-alkyl, orthe radicals R³ and R⁸ together form a methylene or ethylene group,R⁴ and R⁷ independently of one another are hydrogen, methyl or ethyl,R⁵ and R⁶ independently of one another are hydrogen, methyl or ethyl,

X is OR⁹, OCOR⁹, OSO₂R¹⁰,

R⁹ is cyclopropylmethyl or (C₁-C₆)-alkyl substituted by s methoxy orethoxy groups,R¹⁰ is (C₁-C₆)-alkyl substituted by s methoxy or ethoxy groups,Y is (C₁-C₃)-haloalkyl,n is 0, 1 or 2,s is 0, 1, 2 or 3.

Particular preference is given to compounds of the formula (I) in which

R¹ is methyl, ethyl, n-propyl or isopropyl,R² is hydroxyl,R³ and R⁸ independently of one another are hydrogen, methyl or ethyl, orthe radicals R³ and R⁸ together form a methylene or ethylene group,R⁴ and R⁷ independently of one another are hydrogen, methyl or ethyl,R⁵ and R⁶ independently of one another are hydrogen, methyl or ethyl,

X is OR⁹,

R⁹ is cyclopropylmethyl or ethyl or methyl substituted by s methoxy orethoxy groups,Y is trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethylor heptafluoroisopropyl,n is 0, 1 or 2,s is 0, 1, 2 or 3.

In all of the formulae below, the substituents and symbols have the samedefinition as described under formula (I), unless otherwise defined.

Compounds according to the invention in which R² is hydroxyl may beprepared, for example, by the method indicated in scheme 1, byconverting a benzoic acid (II) into an acid chloride or an ester (III),subsequent base-catalyzed reaction with a cyclohexanedione (IV) andsubsequent rearrangement in the presence of a cyanide source. Suchmethods are known to the person skilled in the art and are described,for example, in WO 03/084912. In formula (III), L¹ is chlorine, bromineor alkoxy.

The cyclohexanediones of the formula (IV) are known and can be prepared,for example, according to the methods described in EP 0 338 992.

Compounds according to the invention in which R² has a meaning otherthan that of hydroxyl can be prepared in accordance with scheme 2 fromthe compounds according to the invention in which R² is hydroxyl, byhalogenation and subsequent exchange reactions. Such reactions, whichare known to the person skilled in the art, are described, for example,in WO 03/084912.

The benzoic acids (II) can be prepared from the compounds (VI) byreactions known to the person skilled in the art, for example accordingto scheme 3.

For instance, compounds of the formula (VI) in which L² is anortho-directing substituent such as fluorine can be metallated withlithium diisopropylamide and then reacted with a thiolating reagent togive a compound of the formula (VII). A further metallation reaction,for example with n-butyllithium, and subsequent carboxylation yieldsbenzoic acid (VII). Such reactions are known, for example, fromTetrahedron Letters 1992 (33), 49, pp. 7499-7502; J. Heterocyclic Chem.1999, 36, p. 1453 ff. and Angew. Chem. 2005, 117, 380-398. The radicalL² is then, if appropriate after esterification, exchanged for theradical OR⁹. By reaction of the compounds (X) or (II) with oxidizingagents such as meta-chloroperbenzoic acid, the thio group is oxidized toa sulfinyl or sulfonyl group.

According to scheme 4, an exchange of group L² for OR⁹ can also becarried out at the stage of the benzoylcyclohexanediones.

According to scheme 5, the thio radical in position 3 can also beintroduced via metallation reactions from compounds (VI). Such reactionsare known, for example, from Synthesis 2006, 10, 1578-1589; Org. Lett. 8(2006) 4, 765-768 and Angew. Chem. 2005, 117, 380-398.

According to scheme 6, compounds (II) in which X is hydroxyl can betransferred by acylation reactions into compounds (II) in which X isOCOR⁹ or OSO₂R¹⁰. Such reactions are known, for example, fromHouben-Weyl, Methoden der Organischen Chemie [Methods of OrganicChemistry], Georg Thieme Verlag Stuttgart, Vol. VIII, 4^(th) edition1952, p. 543 ff. and Vol. IX, fourth edition 1955, p. 388 f.

The alkylthio radical in position 3 can be oxidized to the sulfoxide orsulfone. Suitable for this purpose are a number of oxidation systems,for example peracids, such as meta-chloroperbenzoic acid, which areoptionally generated in situ (for example peracetic acid in the systemacetic acid/hydrogen peroxide/sodium tungstate(VI)). Such reactions areknown, for example, from Houben-Weyl, Methoden der Organischen Chemie,Georg Thieme Verlag Stuttgart, Vol. E 11, additional and supplementaryvolumes to the fourth edition 1985, p. 702 ff., p. 718 ff. and p. 1194ff. These oxidation reactions can also be carried out at the stage ofthe benzoylcyclohexanediones or the corresponding enol esters, seescheme 7.

It may be advantageous to change the order of the reaction stepsdescribed in the schemes above, or else to combine them with oneanother. Work-up of the respective reaction mixtures is generallycarried out by known processes, for example by crystallization,aqueous-extractive work-up, by chromatographic methods or by acombination of these methods.

The compounds of the formula (II) are novel and also form part of thesubject matter of the present invention.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the aforementioned reactions can also be preparedin a parallel manner, it being possible for this to take place in amanual, partly automated or completely automated manner. In thisconnection, it is, for example, possible to automate the reactionprocedure, the work-up or the purification of the products and/orintermediates. Overall, this is understood as meaning a procedure asdescribed, for example, by D. Tiebes in CombinatorialChemistry—Synthesis, Analysis, Screening (editor Günther Jung), VerlagWiley 1999, on pages 1 to 34.

For the parallel reaction procedure and work-up, it is possible to use aseries of commercially available instruments, for example Calpysoreaction blocks from Barnstead International, Dubuque, Iowa 52004-0797,USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex,CB 11 3AZ, England or MultiPROBE Automated Workstations from PerkinElmer, Waltham, Mass. 02451, USA. For the parallel purification ofcompounds of the formula (I) and salts thereof or of intermediatesproduced during the preparation, there are available, inter alia,chromatography apparatuses, for example from ISCO, Inc., 4700 SuperiorStreet, Lincoln, Nebr. 68504, USA.

The apparatuses listed lead to a modular procedure in which theindividual process steps are automated, but between the process stepsmanual operations have to be carried out. This can be circumvented byusing partly or completely integrated automation systems in which therespective automation modules are operated, for example, by robots.Automation systems of this type can be acquired, for example, fromCaliper, Hopkinton, Mass. 01748, USA.

The implementation of single or several synthesis steps can be supportedthrough the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described here, the preparation of compounds of theformula (I) and salts thereof can take place completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bonded to a synthesis resin.Solid-phase supported synthesis methods are sufficiently described inthe specialist literature, e.g. Barry A. Bunin in “The CombinatorialIndex”, Verlag Academic Press, 1998 and Combinatorial—Synthesis,Analysis, Screening (editor Günther Jung), Verlag Wiley, 1999. The useof solid-phase supported synthesis methods permits a series of protocolsknown in the literature, which again can be carried out manually or inan automated manner. The reactions can be carried out, for example, bymeans of IRORI technology in microreactors from Nexus Biosystems, 12140Community Road, Poway, Calif. 92064, USA.

Both on a solid phase and in liquid phase can the procedure ofindividual or several synthesis steps be supported through the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editor C. O. Kappe and A. Stadler), Verlag Wiley,2005.

The preparation according to the process described here producescompounds of the formula (I) and their salts in the form of substancecollections which are called libraries. The present invention alsoprovides libraries which comprise at least two compounds of the formula(I) and their salts.

The compounds of the formula (I) according to the invention (and/ortheir salts), hereinbelow also referred to together as “compoundsaccording to the invention”, have excellent herbicidal efficacy againsta broad spectrum of economically important monocotyledonous anddicotyledonous annual harmful plants. The active compounds actefficiently even on perennial weeds which produce shoots from rhizomes,root stocks and other perennial organs and which are difficult tocontrol.

The present invention therefore also relates to a method of controllingunwanted plants or for regulating the growth of plants, preferably incrops of plants, where one or more compound(s) according to theinvention is/are applied to the plants (for example harmful plants suchas monocotyledonous or dicotyledonous weeds or undesired crop plants),to the seeds (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds) or to the area on which the plants grow(for example the area under cultivation). In this context, the compoundsaccording to the invention can be applied for example pre-sowing (ifappropriate also by incorporation into the soil), pre-emergence orpost-emergence. Specific examples may be mentioned of somerepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the compounds according to the invention,without the enumeration being restricted to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

If the compounds according to the invention are applied to the soilsurface before germination, the weed seedlings are either preventedcompletely from emerging or else the weeds grow until they have reachedthe cotyledon stage, but then their growth stops, and, eventually, afterthree to four weeks have elapsed, they die completely.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth stops after the treatment, and the harmful plantsremain at the growth stage of the point of time of application, or theydie completely after a certain time, so that in this manner competitionby the weeds, which is harmful to the crop plants, is eliminated veryearly and in a sustained manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, ormonocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, in particular Zea and Triticum, are damaged only to aninsignificant extent, or not at all, depending on the structure of therespective compound according to the invention and its application rate.This is why the present compounds are highly suitable for the selectivecontrol of unwanted plant growth in plant crops such as agriculturallyuseful plants or ornamentals.

Moreover, the compounds according to the invention (depending on theirrespective structure and the application rate applied) have outstandinggrowth-regulatory properties in crop plants. They engage in the plantmetabolism in a regulatory fashion and can therefore be employed for theinfluencing, in a targeted manner, of plant constituents and forfacilitating harvesting, such as, for example, by triggering desiccationand stunted growth. Moreover, they are also suitable for generallycontrolling and inhibiting unwanted vegetative growth without destroyingthe plants in the process. Inhibiting the vegetative growth plays animportant role in many monocotyledonous and dicotyledonous crops sincefor example lodging can be reduced, or prevented completely, hereby.

By virtue of their herbicidal and plant-growth-regulatory properties,the active compounds can also be employed for controlling harmful plantsin crops of genetically modified plants or plants modified byconventional mutagenesis. In general, the transgenic plants aredistinguished by especially advantageous properties, for example byresistances to certain pesticides, mainly certain herbicides,resistances to plant diseases or causative organisms of plant diseases,such as certain insects or microorganisms such as fungi, bacteria orviruses. Other specific characteristics relate, for example, to theharvested material with regard to quantity, quality, storeability,composition and specific constituents. Thus, transgenic plants are knownwhose starch content is increased, or whose starch quality is altered,or those where the harvested material has a different fatty acidcomposition.

It is preferred, with regard to transgenic crops, to use the compoundsaccording to the invention in economically important transgenic crops ofuseful plants and ornamentals, for example of cereals such as wheat,barley, rye, oats, millet, rice and corn or else crops of sugar beet,cotton, soybean, oilseed rape, potato, tomato, peas and othervegetables. It is preferred to employ the compounds according to theinvention as herbicides in crops of useful plants which are resistant,or have been made resistant by recombinant means, to the phytotoxiceffects of the herbicides.

It is preferred to use the compounds according to the invention or theirsalts in economically important transgenic crops of useful plants andornamentals, for example of cereals such as wheat, barley, rye, oats,millet, rice, cassaya and corn or else crops of sugar beet, cotton,soybean, oilseed rape, potato, tomato, peas and other vegetables. It ispreferred to employ the compounds according to the invention asherbicides in crops of useful plants which are resistant, or have beenmade resistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional methods of generating novel plants which have modifiedproperties in comparison to plants occurring to date consist, forexample, in traditional breeding methods and the generation of mutants.Alternatively, novel plants with altered properties can be generatedwith the aid of recombinant methods (see, for example, EP-A-0221044,EP-A-0131624). For example, the following have been described in severalcases:

-   -   the modification, by recombinant technology, of crop plants with        the aim of modifying the starch synthesized in the plants (for        example WO 92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate type (cf., for example, EP-A-0242236,        EP-A-242246) or of the glyphosate type (WO 92/00377) or of the        sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, with the capability        of producing Bacillus thuringiensis toxins (Bt toxins), which        make the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972).    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are distinguished by higher yields        or better quality,    -   transgenic crop plants which are distinguished by a combination,        for example of the abovementioned novel properties (“gene        stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1(1996) 423-431).

To carry out such recombinant manipulations, nucleic acid moleculeswhich allow mutagenesis or sequence changes by recombination of DNAsequences can be introduced into plasmids. For example, basesubstitutions can be carried out, part-sequences can be removed, ornatural or synthetic sequences may be added with the aid of standardmethods. To link the DNA fragments with one another, it is possible toadd adapters or linkers to the fragments; see, for example, Sambrook etal., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold SpringHarbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Geneand Klone”, VCH Weinheim 2nd ed., 1996.

For example, the generation of plant cells with a reduced activity of agene product can be achieved by expressing at least one correspondingantisense RNA, a sense RNA for achieving a cosuppression effect or byexpressing at least one suitably constructed ribozyme which specificallycleaves transcripts of the above-mentioned gene product. To this end, itis possible to use DNA molecules which encompass the entire codingsequence of a gene product inclusive of any flanking sequences which maybe present, and also DNA molecules which only encompass portions of thecoding sequence, it being necessary for these portions to be long enoughto have an antisense effect in the cells. The use of DNA sequences whichhave a high degree of homology to the coding sequences of a geneproduct, but are not completely identical to them, is also possible.

When expressing nucleic acid molecules in plants, the proteinsynthesized can be localized in any desired compartment of the plantcell. However, to achieve localization in a particular compartment, itis possible, for example, to link the coding region with DNA sequenceswhich ensure localization in a particular compartment. Such sequencesare known to those skilled in the art (see, for example, Braun et al.,EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Thenucleic acid molecules can also be expressed in the organelles of theplant cells.

The transgenic plant cells can be regenerated by known techniques togive rise to entire plants. In principle, the transgenic plants can beplants of any desired plant species, i.e. not only monocotyledonous, butalso dicotyledonous, plants.

Thus, transgenic plants can be obtained whose properties are altered byoverexpression, suppression or inhibition of homologous (=natural) genesor gene sequences or the expression of heterologous (=foreign) genes orgene sequences.

It is preferred to employ the compounds according to the invention intransgenic crops which are resistant to growth regulators such as, forexample, dicamba, or to herbicides which inhibit essential plantenzymes, for example acetolactate synthases (ALS), EPSP synthases,glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD),or to herbicides from the group of the sulfonylureas, the glyphosates,glufosinates or benzoylisoxazoles and analogous active compounds.

When the active compounds according to the invention are used intransgenic crops, effects are frequently observed—in addition to theeffects on harmful plants which can be observed in other crops—which arespecific for the application in the transgenic crop in question, forexample a modified or specifically widened spectrum of weeds which canbe controlled, modified application rates which may be employed forapplication, preferably good combinability with the herbicides to whichthe transgenic crop is resistant, and an effect on growth and yield ofthe transgenic crop plants.

The invention therefore also relates to the use of the compoundsaccording to the invention as herbicides for controlling harmful plantsin transgenic crop plants.

The compounds according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways according to which biological and/or physicochemical parameters arerequired. Possible formulations include, for example: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for scattering and soil application, granules (GR) in the formof microgranules, spray granules, coated granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes. These individual types offormulation are known in principle and are described, for example, in:Winnacker-Küchler, “Chemische Technologie” [Chemical technology], Volume7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “SprayDrying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed.1986.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleylmethyltauride. Toprepare the wettable powders, the herbicidally active compounds areground finely, for example in customary apparatus such as hammer mills,blower mills and air-jet mills and simultaneously or subsequently mixedwith the formulation assistants.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore surfactants of the ionic and/or nonionic type (emulsifiers). Theemulsifiers used may, for example, be: calcium alkylarylsulfonate saltssuch as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finelydistributed solid substances, for example talc, natural clays, such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants, as have, forexample, already been listed above for the other formulation types.

Granules can be prepared either by spraying the active compound ontogranular inert material capable of adsorption or by applying activecompound concentrates to the surface of carrier substances, such assand, kaolinites or granular inert material, by means of adhesives, forexample polyvinyl alcohol, sodium polyacrylate or mineral oils. Suitableactive compounds can also be granulated in the manner customary for thepreparation of fertilizer granules—if desired as a mixture withfertilizers.

Water-dispersible granules are prepared generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the preparation of pan, fluidized bed, extruder and spray granules,see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G.Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical andEngineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”,5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of compounds accordingto the invention. In wettable powders, the active compound concentrationis, for example, from about 10 to 90% by weight, the remainder to 100%by weight consisting of customary formulation components. In the case ofemulsifiable concentrates, the active compound concentration can be fromabout 1 to 90, preferably from 5 to 80, % by weight. Formulations in theform of dusts comprise from 1 to 30% by weight of active compound,preferably usually from 5 to 20% by weight of active compound; sprayablesolutions contain from about 0.05 to 80% by weight, preferably from 2 to50% by weight of active compound. In the case of water-dispersiblegranules, the active compound content depends partially on whether theactive compound is present in liquid or solid form and on whichgranulation auxiliaries, fillers, etc., are used. In thewater-dispersible granules, the content of active compound is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary adhesives, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

Based on these formulations, it is also possible to produce combinationswith other pesticidally active compounds, such as, for example,insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

Active compounds which can be employed in combination with the compoundsaccording to the invention in mixed formulations or in the tank mix are,for example, known active compounds which are based on the inhibitionof, for example, acetolactate synthase, acetyl-CoA carboxylase,cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutaminesynthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase,photosystem I, photosystem II, protoporphyrinogen oxidase, as aredescribed in, for example, Weed Research 26 (1986) 441-445 or “ThePesticide Manual”, 14th edition, The British Crop Protection Council andthe Royal Soc. of Chemistry, 2003 and the literature cited therein.Known herbicides or plant growth regulators which can be combined withthe compounds according to the invention are, for example, the followingactive compounds (the compounds are either designated by the common nameaccording to the International Organization for Standardization (ISO) orby the chemical name, or by the code number) and always comprise all useforms such as acids, salts, esters and isomers such as stereoisomers andoptical isomers. Here, by way of example, one and in some cases aplurality of use forms are mentioned:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen,acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim,alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron,aminocyclopyrachlor, aminopyralid, amitrole, ammonium sulfamate,ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron,aziprotryn, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H,BAS-800H, beflubutamid, benazolin, benazolin-ethyl, bencarbazone,benfluralin, benfuresate, bensulide, bensulfuron-methyl, bentazone,benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop,bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac,bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil,bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos,butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide,carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben,chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac,chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl,chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat chloride,chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron,chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron,clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone,clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl,cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron,cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine,cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet,n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate,dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop,diclofop-methyl, diclofop-P-methyl, diclosulam, diethatyl,diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr,diflufenzopyr-sodium, dimefuron, dikegulac-sodium, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, diquat dibromide, dithiopyr, diuron, DNOC,eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin,ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate,ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide,fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid,glufosinate, L-glufosinate, L-glufosinate-ammonium,glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201,halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02,imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan,indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA),iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ipfencarbazone,isocarbamid, isopropalin, isoproturon, isouron, isoxaben,isoxachlortole, isoxaflutole, isoxapyrifop, IDH-100, KUH-043, KUH-071,karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide,MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium,mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,metazosulfuron, methazole, methiozolin, methoxyphenone, methyldymron,1-methylcyclopropene, methyl isothiocyanate, metobenzuron, metobenzuron,metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron,metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide,monocarbamide, monocarbamide dihydrogensulfate, monolinuron,monosulfuron, monuron, MT 128, MT-5950, i.e.N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011,naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolate-sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat, paraquatdichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin,penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen,pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor,primisulfuron, primisulfuron-methyl, probenazole, profluazol,procyazine, prodiamine, prifluraline, profoxydim, prohexadione,prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin,prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen,pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate),pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl,pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid,pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil,secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279,sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron,sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron,SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene,tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb,terbuchlor, terbumeton, terbuthylazine, terbutryn, TH-547, thenylchlor,thiafluamide, thiazafluoron, thiazopyr, thidiazimin, thidiazuron,thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone,tralkoxydim, triallate, triasulfuron, triaziflam, triazofenamide,tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr,tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium,trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon,trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole,uniconazole-P, vernolate, ZJ-0166, ZJ-0270, ZJ-0543, ZJ-0862 and thefollowing compounds

For application, the formulations present in commercial form are, ifappropriate, diluted in a customary manner, for example in the case ofwettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules with water. Preparations in the form ofdusts, granules for soil application or granules for broadcasting andsprayable solutions are usually not diluted further with other inertsubstances prior to application.

The required application rate of the compounds of the formula (I) variesaccording to the external conditions such as, inter alia, temperature,humidity and the type of herbicide used. It may vary within wide limits,for example between 0.001 and 1.0 kg/ha or more of active substance;however, preferably it is between 0.005 and 750 g/ha.

The examples below illustrate the invention:

A. CHEMICAL EXAMPLES2-(2-Methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione(Table Example No. 1-17) Step 1: Synthesis of1-fluoro-2-methylthio-3-(trifluoromethyl)benzene

Under an atmosphere of inert gas, 32.8 ml (1.6 M in hexane, 52.5 mmol)of n-butyllithium were added dropwise to a solution, cooled to 0° C., of7.77 ml (55 mmol) of diisopropylamine in 100 ml of anhydrous THF, andafter 10 minutes of stirring the solution was cooled to −78° C. 8.21 g(50 mmol) of 3-fluorobenzotrifluoride were added at this temperature,and the reaction mixture was stirred at this temperature for 1 h. 4.21ml (55 mmol) of dimethyl disulfide were then added dropwise. Withinabout 3 h, the reaction mixture had warmed to room temperature (RT), andit was then once more cooled to 0° C. At this temperature, 10 ml ofwater were added dropwise, and the reaction mixture was concentrated toabout ¼ of its volume. The residue was taken up in water anddichloromethane, the phases were separated and the organic phase waswashed successively with water, 10 percent strength hydrochloric acid,water, saturated aqueous NaHCO₃ solution, water and saturated aqueousNaCl solution and dried over sodium sulfate and filtered. The solventwas removed and the residue was rectified under reduced pressure. Thisgave 8 g of 1-fluoro-2-methylthio-3-(trifluoromethyl)benzene of aboiling point of 68° C. at 6 mm Hg.

Step 2: Synthesis of 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoicacid

Under an atmosphere of inert gas, 27.5 ml (1.6 M in hexane, 44 mmol) ofn-butyllithium were added dropwise to a solution, cooled to −78° C., of7.98 g (38 mmol) of 1-fluoro-2-methylthio-3-(trifluoromethyl)benzene in60 ml of anhydrous THF, where the temperature of the reaction mixtureshould not exceed −65° C. The mixture was stirred at −78° C. for 3 h,and at this temperature a carbon dioxide stream was then introduced suchthat the temperature of the reaction mixture did not exceed −45° C. Themixture was then warmed to RT and then once more cooled to 0° C. Forwork-up, water was added dropwise at this temperature until theprecipitate formed had dissolved. Diethyl ether was added, and theorganic phase was extracted three times with water. The combined aqueousphases were acidified with 10 percent strength hydrochloric acid. Theaqueous phase was extracted repeatedly with dichloromethane, thecombined organic phases were washed with saturated aqueous NaCl solutionand dried over sodium sulfate and the filtrate was then freed from thesolvent. The crude product obtained in this manner was thenrecrystallized from gasoline (80-110° C.)/ethyl acetate. This gave 6.8 gof 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid.

Step 3: Synthesis of methyl2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate

5 ml of concentrated sulfuric acid were added to 20.0 g (78.7 mmol) of2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid in 200 ml ofmethanol, and the mixture was heated under reflux until HPLC analysisshowed complete conversion. The mixture was cooled and the solvent wasremoved. The residue was taken up in water, and the mixture wasextracted twice with ethyl acetate. The combined organic phases werewashed once with saturated aqueous NaHCO₃ solution. Finally, the organicphase was dried and the filtrate was concentrated. This gave 20.5 g ofmethyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate.

Step 4: Synthesis of methyl2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate

A mixture of 19.9 g (74.2 mmol) of methyl2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate and 40.1 g (30% byweight, 223 mmol) of sodium methoxide in 250 ml of methanol was heatedunder reflux for 6 h. For work-up, the mixture was concentrated on arotary evaporator, the residue was taken up in water and the mixture wasextracted with dichloromethane. The organic phase was dried and thefiltrate was freed from the solvent. This gave 15.9 g of methyl2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue. Theaqueous phase from the extractive work-up was acidified with dilutehydrochloric acid and extracted with ethyl acetate. The organic phasewas dried and the filtrate was freed from the solvent. This gave anadditional 3.80 g of methyl2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue.

Step 5: Synthesis of 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoicacid (Table Example No. 12-13)

16 ml of 20 percent strength aqueous sodium hydroxide solution wereadded to 16.0 g (57.1 mmol) of methyl2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate in 160 ml ofmethanol, and the mixture was stirred at RT for 4 h. For work-up, themixture was freed from the solvent and the residue was taken up in alittle water. The mixture was cooled in an ice bath and then acidifiedwith dilute hydrochloric acid. The mixture was stirred at RT for 5 min,and the contents was then filtered. This gave 15.3 g of2-methoxy-3-methylthio-4-(trifluoromethyl)benzoic acid.

Step 6: Synthesis of3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone

133 mg (1.05 mmol) of oxalyl dichloride and three drops ofN,N-dimethylformamide were added in succession to 200 mg (purity 78% byweight, 0.59 mmol) of 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoicacid in 20 ml of dichloromethane. After the elimination of gas hadceased, the mixture was heated under reflux for another 10 min. Thecontent was then cooled to RT and freed from the solvent. 93 mg (0.83mmol) of 1,3-cyclohexanedione were added to the residue in 20 ml of drydichloromethane, and 152 mg (1.50 mmol) of triethylamine were then addeddropwise. The mixture was stirred at RT for 16 h. For work-up, 3 ml of1M hydrochloric acid were added to the contents. After phase separation,the organic phase was freed from the solvent. The residue was purifiedchromatographically, which isolated 100 mg of3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone.

Step 7: Synthesis of3-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enone

68 mg (70% by weight, 0.28 mmol) of meta-chloroperbenzoic acid wereadded to 100 mg (0.28 mmol) of3-(2-methoxy-3-methylthio-4-(trifluoromethyl)benzoyloxy)-cyclohex-2-enonein 10 ml of dichloromethane. The mixture was stirred at RT for 1 h. Forwork-up, 3 ml of 10 percent strength aqueous sodium hydrogensulfitesolution were added. After confirmation that no peroxides were present,the organic phase was washed twice with in each case 5 ml of saturatedaqueous NaHCO₃ solution. After phase separation, the solvent wasremoved. This gave 90 mg of3-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyloxy)cyclohex-2-enone.

Step 8: Synthesis of2-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyl)-cyclohexane-1,3-dione(Table Example No. 1-17)

48 mg (0.48 mmol) of triethylamine and eight drops of trimethylsilylcyanide were successively added to 90 mg (0.24 mmol) of3-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyloxy)cyclohex-2-enonein 15 ml of acetonitrile. The mixture was stirred at RT for 16 h. Forwork-up, the solvent was removed. The residue was taken up in 15 ml ofdichloromethane, and 3 ml of 1 N hydrochloric acid were added. Afterphase separation, the solvent was removed and the residue was purifiedchromatographically, which gave 49.9 mg of2-(2-methoxy-3-methylsulfinyl-4-(trifluoromethyl)benzoyl)cyclohexane-1,3-dione.

The examples listed in the tables below were prepared analogously to themethods mentioned above or can be obtained analogously to the methodsmentioned above. These compounds are very particularly preferred.

The abbreviations used denote:

Et = ethyl Me = methyl Pr = propyl Ph = phenyl

TABLE 1 Compounds of the formula (I) according to the invention in whichR² is hydroxyl and R³ to R⁸ are each hydrogen. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 1-1 OH Me 0 CF₃ 1-2 OH Et0 CF₃ 1-3 OH n-Pr 0 CF₃ 1-4 OH i-Pr 0 CF₃ 1-5 OH Me 1 CF₃ 1-6 OH Et 1CF₃ 1-7 OH n-Pr 1 CF₃ 1-8 OH i-Pr 1 CF₃ 1-9 OH Me 2 CF₃ 1-10 OH Et 2 CF₃1-11 OH n-Pr 2 CF₃ 1-12 OH i-Pr 2 CF₃ 1-13 OMe Me 0 CF₃ 16.93 (s, 1H),7.49 (d, 1H), 7.18 (d, 1H), 3.86 (s, 3H), 2.78 (t, 2H), 2.43 (t, 2H),2.42 (s, 3H), 2.06 (quint, 2H) 1-14 OMe Et 0 CF₃ 1-15 OMe n-Pr 0 CF₃1-16 OMe i-Pr 0 CF₃ 1-17 OMe Me 1 CF₃ 16.66 (s, 1H), 7.56 (d, 1H), 7.42(d, 1H), 3.88 (s, 3H), 3.07 (s, 3H), 2.81 (m, 2H), 2.46 (m, 2H), 2.08(m, 2H) 1-18 OMe Et 1 CF₃ 1-19 OMe n-Pr 1 CF₃ 1-20 OMe i-Pr 1 CF₃ 1-21OMe Me 2 CF₃ 16.67 (s, 1H), 7.71 (d, 1H), 7.51 (d, 1H), 3.84 (s, 3H),3.30 (s, 3H), 2.82 (t, 2H), 2.44 (t, 2H), 2.08 (quint, 2H) 1-22 OMe Et 2CF₃ 1-23 OMe n-Pr 2 CF₃ 1-24 OMe i-Pr 2 CF₃ 1-25 OEt Me 0 CF₃ 16.82 (s,1H), 7.47 (d, 1H), 7.22 (d, 1H), 4.03 (q, 2H), 2.76 (t, 2H), 2.46-2.41(m, 5H), 2.06 (quint, 2H), 1.30 (t, 3H) 1-26 OEt Et 0 CF₃ 1-27 OEt n-Pr0 CF₃ 1-28 OEt i-Pr 0 CF₃ 1-29 OEt Me 1 CF₃ 16.66 (s, 1H), 7.55 (d, 1H),7.41 (d, 1H), 4.30 (m, 1H), 3.78 (m, 1H), 3.06 (s, 3H), 2.80 (m, 2H),2.52 (m, 1H), 2.39 (m, 1 H), 2.07 (m, 2H), 1.32 (t, 3H) 1-30 OEt Et 1CF₃ 1-31 OEt n-Pr 1 CF₃ 1-32 OEt i-Pr 1 CF₃ 1-33 OEt Me 2 CF₃ 16.63 (s,1H), 7.71 (d, 1H), 7.51 (d, 1H), 4.01 (m, 2H), 3.32 (s, 3H), 2.81 (t,2H), 2.44 (t, 2H), 2.07 (quint, 2H), 1.32 (t, 3H) 1-34 OEt Et 2 CF₃ 1-35OEt n-Pr 2 CF₃ 1-36 OEt i-Pr 2 CF₃ 1-37 O—CH₂—c-Pr Me 0 CF₃ 1-38O—CH₂—c-Pr Et 0 CF₃ 1-39 O—CH₂—c-Pr n-Pr 0 CF₃ 1-40 O—CH₂—c-Pr i-Pr 0CF₃ 1-41 O—CH₂—c-Pr Me 1 CF₃ 1-42 O—CH₂—c-Pr Et 1 CF₃ 1-43 O—CH₂—c-Prn-Pr 1 CF₃ 1-44 O—CH₂—c-Pr i-Pr 1 CF₃ 1-45 O—CH₂—c-Pr Me 2 CF₃ 1-46O—CH₂—c-Pr Et 2 CF₃ 1-47 O—CH₂—c-Pr n-Pr 2 CF₃ 1-48 O—CH₂—c-Pr i-Pr 2CF₃ 1-49 OCH₂CH₂OMe Me 0 CF₃ 1-50 OCH₂CH₂OMe Et 0 CF₃ 1-51 OCH₂CH₂OMen-Pr 0 CF₃ 1-52 OCH₂CH₂OMe i-Pr 0 CF₃ 1-53 OCH₂CH₂OMe Me 1 CF₃ 1-54OCH₂CH₂OMe Et 1 CF₃ 1-55 OCH₂CH₂OMe n-Pr 1 CF₃ 1-56 OCH₂CH₂OMe i-Pr 1CF₃ 1-57 OCH₂CH₂OMe Me 2 CF₃ 1-58 OCH₂CH₂OMe Et 2 CF₃ 1-59 OCH₂CH₂OMen-Pr 2 CF₃ 1-60 OCH₂CH₂OMe i-Pr 2 CF₃ 1-61 OCH₂CH₂SMe Me 0 CF₃ 1-62OCH₂CH₂SMe Et 0 CF₃ 1-63 OCH₂CH₂SMe n-Pr 0 CF₃ 1-64 OCH₂CH₂SMe i-Pr 0CF₃ 1-65 OCH₂CH₂SMe Me 1 CF₃ 1-66 OCH₂CH₂SMe Et 1 CF₃ 1-67 OCH₂CH₂SMen-Pr 1 CF₃ 1-68 OCH₂CH₂SMe i-Pr 1 CF₃ 1-69 OCH₂CH₂SMe Me 2 CF₃ 1-70OCH₂CH₂SMe Et 2 CF₃ 1-71 OCH₂CH₂SMe n-Pr 2 CF₃ 1-72 OCH₂CH₂SMe i-Pr 2CF₃ 1-73 OCH₂CH₂SO₂Me Me 0 CF₃ 1-74 OCH₂CH₂SO₂Me Et 0 CF₃ 1-75OCH₂CH₂SO₂Me n-Pr 0 CF₃ 1-76 OCH₂CH₂SO₂Me i-Pr 0 CF₃ 1-77 OCH₂CH₂SO₂MeMe 1 CF₃ 1-78 OCH₂CH₂SO₂Me Et 1 CF₃ 1-79 OCH₂CH₂SO₂Me n-Pr 1 CF₃ 1-80OCH₂CH₂SO₂Me i-Pr 1 CF₃ 1-81 OCH₂CH₂SO₂Me Me 2 CF₃ 1-82 OCH₂CH₂SO₂Me Et2 CF₃ 1-83 OCH₂CH₂SO₂Me n-Pr 2 CF₃ 1-84 OCH₂CH₂SO₂Me i-Pr 2 CF₃ 1-85OCOMe Me 0 CF₃ 1-86 OCOMe Et 0 CF₃ 1-87 OCOMe n-Pr 0 CF₃ 1-88 OCOMe i-Pr0 CF₃ 1-89 OCOMe Me 1 CF₃ 1-90 OCOMe Et 1 CF₃ 1-91 OCOMe n-Pr 1 CF₃ 1-92OCOMe i-Pr 1 CF₃ 1-93 OCOMe Me 2 CF₃ 1-94 OCOMe Et 2 CF₃ 1-95 OCOMe n-Pr2 CF₃ 1-96 OCOMe i-Pr 2 CF₃ 1-97 OSO₂Me Me 0 CF₃ 1-98 OSO₂Me Et 0 CF₃1-99 OSO₂Me n-Pr 0 CF₃ 1-100 OSO₂Me i-Pr 0 CF₃ 1-101 OSO₂Me Me 1 CF₃1-102 OSO₂Me Et 1 CF₃ 1-103 OSO₂Me n-Pr 1 CF₃ 1-104 OSO₂Me i-Pr 1 CF₃1-105 OSO₂Me Me 2 CF₃ 1-106 OSO₂Me Et 2 CF₃ 1-107 OSO₂Me n-Pr 2 CF₃1-108 OSO₂Me i-Pr 2 CF₃ 1-109 OMe Me 0 C₂F₅ 1-110 OMe Et 0 C₂F₅ 1-111OMe n-Pr 0 C₂F₅ 1-112 OMe i-Pr 0 C₂F₅ 1-113 OMe Me 1 C₂F₅ 1-114 OMe Et 1C₂F₅ 1-115 OMe n-Pr 1 C₂F₅ 1-116 OMe i-Pr 1 C₂F₅ 1-117 OMe Me 2 C₂F₅1-118 OMe Et 2 C₂F₅ 1-119 OMe n-Pr 2 C₂F₅ 1-120 OMe i-Pr 2 C₂F₅ 1-121OEt Me 0 C₂F₅ 1-122 OEt Et 0 C₂F₅ 1-123 OEt n-Pr 0 C₂F₅ 1-124 OEt i-Pr 0C₂F₅ 1-125 OEt Me 1 C₂F₅ 1-126 OEt Et 1 C₂F₅ 1-127 OEt n-Pr 1 C₂F₅ 1-128OEt i-Pr 1 C₂F₅ 1-129 OEt Me 2 C₂F₅ 1-130 OEt Et 2 C₂F₅ 1-131 OEt n-Pr 2C₂F₅ 1-132 OEt i-Pr 2 C₂F₅ 1-133 O—CH₂—c-Pr Me 0 C₂F₅ 1-134 O—CH₂—c-PrEt 0 C₂F₅ 1-135 O—CH₂—c-Pr n-Pr 0 C₂F₅ 1-136 O—CH₂—c-Pr i-Pr 0 C₂F₅1-137 O—CH₂—c-Pr Me 1 C₂F₅ 1-138 O—CH₂—c-Pr Et 1 C₂F₅ 1-139 O—CH₂—c-Prn-Pr 1 C₂F₅ 1-140 O—CH₂—c-Pr i-Pr 1 C₂F₅ 1-141 O—CH₂—c-Pr Me 2 C₂F₅1-142 O—CH₂—c-Pr Et 2 C₂F₅ 1-143 O—CH₂—c-Pr n-Pr 2 C₂F₅ 1-144 O—CH₂—c-Pri-Pr 2 C₂F₅ 1-145 OCH₂CH₂OMe Me 0 C₂F₅ 1-146 OCH₂CH₂OMe Et 0 C₂F₅ 1-147OCH₂CH₂OMe n-Pr 0 C₂F₅ 1-148 OCH₂CH₂OMe i-Pr 0 C₂F₅ 1-149 OCH₂CH₂OMe Me1 C₂F₅ 1-150 OCH₂CH₂OMe Et 1 C₂F₅ 1-151 OCH₂CH₂OMe n-Pr 1 C₂F₅ 1-152OCH₂CH₂OMe i-Pr 1 C₂F₅ 1-153 OCH₂CH₂OMe Me 2 C₂F₅ 1-154 OCH₂CH₂OMe Et 2C₂F₅ 1-155 OCH₂CH₂OMe n-Pr 2 C₂F₅ 1-156 OCH₂CH₂OMe i-Pr 2 C₂F₅ 1-157OCH₂CH₂SMe Me 0 C₂F₅ 1-158 OCH₂CH₂SMe Et 0 C₂F₅ 1-159 OCH₂CH₂SMe n-Pr 0C₂F₅ 1-160 OCH₂CH₂SMe i-Pr 0 C₂F₅ 1-161 OCH₂CH₂SMe Me 1 C₂F₅ 1-162OCH₂CH₂SMe Et 1 C₂F₅ 1-163 OCH₂CH₂SMe n-Pr 1 C₂F₅ 1-164 OCH₂CH₂SMe i-Pr1 C₂F₅ 1-165 OCH₂CH₂SMe Me 2 C₂F₅ 1-166 OCH₂CH₂SMe Et 2 C₂F₅ 1-167OCH₂CH₂SMe n-Pr 2 C₂F₅ 1-168 OCH₂CH₂SMe i-Pr 2 C₂F₅ 1-169 OCH₂CH₂SO₂MeMe 0 C₂F₅ 1-170 OCH₂CH₂SO₂Me Et 0 C₂F₅ 1-171 OCH₂CH₂SO₂Me n-Pr 0 C₂F₅1-172 OCH₂CH₂SO₂Me i-Pr 0 C₂F₅ 1-173 OCH₂CH₂SO₂Me Me 1 C₂F₅ 1-174OCH₂CH₂SO₂Me Et 1 C₂F₅ 1-175 OCH₂CH₂SO₂Me n-Pr 1 C₂F₅ 1-176 OCH₂CH₂SO₂Mei-Pr 1 C₂F₅ 1-177 OCH₂CH₂SO₂Me Me 2 C₂F₅ 1-178 OCH₂CH₂SO₂Me Et 2 C₂F₅1-179 OCH₂CH₂SO₂Me n-Pr 2 C₂F₅ 1-180 OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 1-181 OMeMe 0 CCl₃ 1-182 OMe Et 0 CCl₃ 1-183 OMe n-Pr 0 CCl₃ 1-184 OMe i-Pr 0CCl₃ 1-185 OMe Me 1 CCl₃ 1-186 OMe Et 1 CCl₃ 1-187 OMe n-Pr 1 CCl₃ 1-188OMe i-Pr 1 CCl₃ 1-189 OMe Me 2 CCl₃ 1-190 OMe Et 2 CCl₃ 1-191 OMe n-Pr 2CCl₃ 1-192 OMe i-Pr 2 CCl₃ 1-193 OEt Me 0 CCl₃ 1-194 OEt Et 0 CCl₃ 1-195OEt n-Pr 0 CCl₃ 1-196 OEt i-Pr 0 CCl₃ 1-197 OEt Me 1 CCl₃ 1-198 OEt Et 1CCl₃ 1-199 OEt n-Pr 1 CCl₃ 1-200 OEt i-Pr 1 CCl₃ 1-201 OEt Me 2 CCl₃1-202 OEt Et 2 CCl₃ 1-203 OEt n-Pr 2 CCl₃ 1-204 OEt i-Pr 2 CCl₃ 1-205O—CH₂—c-Pr Me 0 CCl₃ 1-206 O—CH₂—c-Pr Et 0 CCl₃ 1-207 O—CH₂—c-Pr n-Pr 0CCl₃ 1-208 O—CH₂—c-Pr i-Pr 0 CCl₃ 1-209 O—CH₂—c-Pr Me 1 CCl₃ 1-210O—CH₂—c-Pr Et 1 CCl₃ 1-211 O—CH₂—c-Pr n-Pr 1 CCl₃ 1-212 O—CH₂—c-Pr i-Pr1 CCl₃ 1-213 O—CH₂—c-Pr Me 2 CCl₃ 1-214 O—CH₂—c-Pr Et 2 CCl₃ 1-215O—CH₂—c-Pr n-Pr 2 CCl₃ 1-216 O—CH₂—c-Pr i-Pr 2 CCl₃ 1-217 OCH₂CH₂OMe Me0 CCl₃ 1-218 OCH₂CH₂OMe Et 0 CCl₃ 1-219 OCH₂CH₂OMe n-Pr 0 CCl₃ 1-220OCH₂CH₂OMe i-Pr 0 CCl₃ 1-221 OCH₂CH₂OMe Me 1 CCl₃ 1-222 OCH₂CH₂OMe Et 1CCl₃ 1-223 OCH₂CH₂OMe n-Pr 1 CCl₃ 1-224 OCH₂CH₂OMe i-Pr 1 CCl₃ 1-225OCH₂CH₂OMe Me 2 CCl₃ 1-226 OCH₂CH₂OMe Et 2 CCl₃ 1-227 OCH₂CH₂OMe n-Pr 2CCl₃ 1-228 OCH₂CH₂OMe i-Pr 2 CCl₃ 1-229 OCH₂CH₂SMe Me 0 CCl₃ 1-230OCH₂CH₂SMe Et 0 CCl₃ 1-231 OCH₂CH₂SMe n-Pr 0 CCl₃ 1-232 OCH₂CH₂SMe i-Pr0 CCl₃ 1-233 OCH₂CH₂SMe Me 1 CCl₃ 1-234 OCH₂CH₂SMe Et 1 CCl₃ 1-235OCH₂CH₂SMe n-Pr 1 CCl₃ 1-236 OCH₂CH₂SMe i-Pr 1 CCl₃ 1-237 OCH₂CH₂SMe Me2 CCl₃ 1-238 OCH₂CH₂SMe Et 2 CCl₃ 1-239 OCH₂CH₂SMe n-Pr 2 CCl₃ 1-240OCH₂CH₂SMe i-Pr 2 CCl₃ 1-241 OCH₂CH₂SO₂Me Me 0 CCl₃ 1-242 OCH₂CH₂SO₂MeEt 0 CCl₃ 1-243 OCH₂CH₂SO₂Me n-Pr 0 CCl₃ 1-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃1-245 OCH₂CH₂SO₂Me Me 1 CCl₃ 1-246 OCH₂CH₂SO₂Me Et 1 CCl₃ 1-247OCH₂CH₂SO₂Me n-Pr 1 CCl₃ 1-248 OCH₂CH₂SO₂Me i-Pr 1 CCl₃ 1-249OCH₂CH₂SO₂Me Me 2 CCl₃ 1-250 OCH₂CH₂SO₂Me Et 2 CCl₃ 1-251 OCH₂CH₂SO₂Men-Pr 2 CCl₃ 1-252 OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 1-253 OMe Me 0 CHF2 1-254 OMeEt 0 CHF2 1-255 OMe n-Pr 0 CHF2 1-256 OMe i-Pr 0 CHF2 1-257 OMe Me 1CHF2 1-258 OMe Et 1 CHF2 1-259 OMe n-Pr 1 CHF2 1-260 OMe i-Pr 1 CHF21-261 OMe Me 2 CHF2 1-262 OMe Et 2 CHF2 1-263 OMe n-Pr 2 CHF2 1-264 OMei-Pr 2 CHF2 1-265 OEt Me 0 CHF2 1-266 OEt Et 0 CHF2 1-267 OEt n-Pr 0CHF2 1-268 OEt i-Pr 0 CHF2 1-269 OEt Me 1 CHF2 1-270 OEt Et 1 CHF2 1-271OEt n-Pr 1 CHF2 1-272 OEt i-Pr 1 CHF2 1-273 OEt Me 2 CHF2 1-274 OEt Et 2CHF2 1-275 OEt n-Pr 2 CHF2 1-276 OEt i-Pr 2 CHF2 1-277 O—CH₂—c-Pr Me 0CHF2 1-278 O—CH₂—c-Pr Et 0 CHF2 1-279 O—CH₂—c-Pr n-Pr 0 CHF2 1-280O—CH₂—c-Pr i-Pr 0 CHF2 1-281 O—CH₂—c-Pr Me 1 CHF2 1-282 O—CH₂—c-Pr Et 1CHF2 1-283 O—CH₂—c-Pr n-Pr 1 CHF2 1-284 O—CH₂—c-Pr i-Pr 1 CHF2 1-285O—CH₂—c-Pr Me 2 CHF2 1-286 O—CH₂—c-Pr Et 2 CHF2 1-287 O—CH₂—c-Pr n-Pr 2CHF2 1-288 O—CH₂—c-Pr i-Pr 2 CHF2 1-289 OCH₂CH₂OMe Me 0 CHF2 1-290OCH₂CH₂OMe Et 0 CHF2 1-291 OCH₂CH₂OMe n-Pr 0 CHF2 1-292 OCH₂CH₂OMe i-Pr0 CHF2 1-293 OCH₂CH₂OMe Me 1 CHF2 1-294 OCH₂CH₂OMe Et 1 CHF2 1-295OCH₂CH₂OMe n-Pr 1 CHF2 1-296 OCH₂CH₂OMe i-Pr 1 CHF2 1-297 OCH₂CH₂OMe Me2 CHF2 1-298 OCH₂CH₂OMe Et 2 CHF2 1-299 OCH₂CH₂OMe n-Pr 2 CHF2 1-300OCH₂CH₂OMe i-Pr 2 CHF2 1-301 OCH₂CH₂SMe Me 0 CHF2 1-302 OCH₂CH₂SMe Et 0CHF2 1-303 OCH₂CH₂SMe n-Pr 0 CHF2 1-304 OCH₂CH₂SMe i-Pr 0 CHF2 1-305OCH₂CH₂SMe Me 1 CHF2 1-306 OCH₂CH₂SMe Et 1 CHF2 1-307 OCH₂CH₂SMe n-Pr 1CHF2 1-308 OCH₂CH₂SMe i-Pr 1 CHF2 1-309 OCH₂CH₂SMe Me 2 CHF2 1-310OCH₂CH₂SMe Et 2 CHF2 1-311 OCH₂CH₂SMe n-Pr 2 CHF2 1-312 OCH₂CH₂SMe i-Pr2 CHF2 1-313 OCH₂CH₂SO₂Me Me 0 CHF2 1-314 OCH₂CH₂SO₂Me Et 0 CHF2 1-315OCH₂CH₂SO₂Me n-Pr 0 CHF2 1-316 OCH₂CH₂SO₂Me i-Pr 0 CHF2 1-317OCH₂CH₂SO₂Me Me 1 CHF2 1-318 OCH₂CH₂SO₂Me Et 1 CHF2 1-319 OCH₂CH₂SO₂Men-Pr 1 CHF2 1-320 OCH₂CH₂SO₂Me i-Pr 1 CHF2 1-321 OCH₂CH₂SO₂Me Me 2 CHF21-322 OCH₂CH₂SO₂Me Et 2 CHF2 1-323 OCH₂CH₂SO₂Me n-Pr 2 CHF2 1-324OCH₂CH₂SO₂Me i-Pr 2 CHF2 1-325 OMe Me 0 CF(CF₃)₂ 1-326 OMe Et 0 CF(CF₃)₂1-327 OMe n-Pr 0 CF(CF₃)₂ 1-328 OMe i-Pr 0 CF(CF₃)₂ 1-329 OMe Me 1CF(CF₃)₂ 1-330 OMe Et 1 CF(CF₃)₂ 1-331 OMe n-Pr 1 CF(CF₃)₂ 1-332 OMei-Pr 1 CF(CF₃)₂ 1-333 OMe Me 2 CF(CF₃)₂ 1-334 OMe Et 2 CF(CF₃)₂ 1-335OMe n-Pr 2 CF(CF₃)₂ 1-336 OMe i-Pr 2 CF(CF₃)₂ 1-337 OEt Me 0 CF(CF₃)₂1-338 OEt Et 0 CF(CF₃)₂ 1-339 OEt n-Pr 0 CF(CF₃)₂ 1-340 OEt i-Pr 0CF(CF₃)₂ 1-341 OEt Me 1 CF(CF₃)₂ 1-342 OEt Et 1 CF(CF₃)₂ 1-343 OEt n-Pr1 CF(CF₃)₂ 1-344 OEt i-Pr 1 CF(CF₃)₂ 1-345 OEt Me 2 CF(CF₃)₂ 1-346 OEtEt 2 CF(CF₃)₂ 1-347 OEt n-Pr 2 CF(CF₃)₂ 1-348 OEt i-Pr 2 CF(CF₃)₂ 1-349O—CH₂—c-Pr Me 0 CF(CF₃)₂ 1-350 O—CH₂—c-Pr Et 0 CF(CF₃)₂ 1-351 O—CH₂—c-Prn-Pr 0 CF(CF₃)₂ 1-352 O—CH₂—c-Pr i-Pr 0 CF(CF₃)₂ 1-353 O—CH₂—c-Pr Me 1CF(CF₃)₂ 1-354 O—CH₂—c-Pr Et 1 CF(CF₃)₂ 1-355 O—CH₂—c-Pr n-Pr 1 CF(CF₃)₂1-356 O—CH₂—c-Pr i-Pr 1 CF(CF₃)₂ 1-357 O—CH₂—c-Pr Me 2 CF(CF₃)₂ 1-358O—CH₂—c-Pr Et 2 CF(CF₃)₂ 1-359 O—CH₂—c-Pr n-Pr 2 CF(CF₃)₂ 1-360O—CH₂—c-Pr i-Pr 2 CF(CF₃)₂ 1-361 OCH₂CH₂OMe Me 0 CF(CF₃)₂ 1-362OCH₂CH₂OMe Et 0 CF(CF₃)₂ 1-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂ 1-364OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 1-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 1-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 1-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 1-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 1-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 1-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 1-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 1-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 1-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 1-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 1-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 1-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 1-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 1-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 1-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 1-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 1-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 1-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 1-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 1-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 1-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 1-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 1-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 1-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 1-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 1-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 1-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 1-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 1-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 1-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 1-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 1-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

TABLE 2 Compounds of the formula (I) according to the invention in whichR² is hydroxyl, R³ to R⁶ are each hydrogen and R⁷ and R⁸ are eachmethyl. (I)

Physical data: ¹H-NMR: δ No. X R¹ n Y [CDCl₃] 2-1 OH Me 0 CF₃ 2-2 OH Et0 CF₃ 2-3 OH n-Pr 0 CF₃ 2-4 OH i-Pr 0 CF₃ 2-5 OH Me 1 CF₃ 2-6 OH Et 1CF₃ 2-7 OH n-Pr 1 CF₃ 2-8 OH i-Pr 1 CF₃ 2-9 OH Me 2 CF₃ 2-10 OH Et 2 CF₃2-11 OH n-Pr 2 CF₃ 2-12 OH i-Pr 2 CF₃ 2-13 OMe Me 0 CF₃ 17.37/16.60 (s,1H), 7.52-7.47 (d/d, 1H), 7.23- 7.18 (m, 1H), 3.83/3.80 (s, 3H),2.79/2.47 (t, 2H), 2.42/2.41 (s, 3H), 1.93- 1.85 (m, 2H), 1.38/1.11 (s,6H) 2-14 OMe Et 0 CF₃ 2-15 OMe n-Pr 0 CF₃ 2-16 OMe i-Pr 0 CF₃ 2-17 OMeMe 1 CF₃ 17.12/16.33 (s, 1H), 7.58/7.55 (d, 1H), 7.50-7.42 (m, 1H),3.86/3.84 (s, 3H), 3.07/ 3.05 (s, 3H), 2.82/ 2.49 (m, 2H), 1.89 (m, 2H),1.42/ 1.21 (s, 3H), 1.37/1.07 (s, 3H) 2-18 OMe Et 1 CF₃ 2-19 OMe n-Pr 1CF₃ 2-20 OMe i-Pr 1 CF₃ 2-21 OMe Me 2 CF₃ 17.13/16.39 (s, 1H), 7.73/7.72(d, 1H), 7.55/7.52 (d, 1H), 3.83/3.82 (s, 3H), 3.29/ 3.27 (s, 3H), 2.82/2.47 (t, 2H), 1.94- 1.87 (m, 2H), 1.41/1.12 (s, 6H) 2-22 OMe Et 2 CF₃2-23 OMe n-Pr 2 CF₃ 2-24 OMe i-Pr 2 CF₃ 2-25 OEt Me 0 CF₃ 2-26 OEt Et 0CF₃ 2-27 OEt n-Pr 0 CF₃ 2-28 OEt i-Pr 0 CF₃ 2-29 OEt Me 1 CF₃ 2-30 OEtEt 1 CF₃ 2-31 OEt n-Pr 1 CF₃ 2-32 OEt i-Pr 1 CF₃ 2-33 OEt Me 2 CF₃ 2-34OEt Et 2 CF₃ 2-35 OEt n-Pr 2 CF₃ 2-36 OEt i-Pr 2 CF₃ 2-37 O—CH₂—c-Pr Me0 CF₃ 2-38 O—CH₂—c-Pr Et 0 CF₃ 2-39 O—CH₂—c-Pr n-Pr 0 CF₃ 2-40O—CH₂—c-Pr i-Pr 0 CF₃ 2-41 O—CH₂—c-Pr Me 1 CF₃ 2-42 O—CH₂—c-Pr Et 1 CF₃2-43 O—CH₂—c-Pr n-Pr 1 CF₃ 2-44 O—CH₂—c-Pr i-Pr 1 CF₃ 2-45 O—CH₂—c-Pr Me2 CF₃ 2-46 O—CH₂—c-Pr Et 2 CF₃ 2-47 O—CH₂—c-Pr n-Pr 2 CF₃ 2-48O—CH₂—c-Pr i-Pr 2 CF₃ 2-49 OCH₂CH₂OMe Me 0 CF₃ 2-50 OCH₂CH₂OMe Et 0 CF₃2-51 OCH₂CH₂OMe n-Pr 0 CF₃ 2-52 OCH₂CH₂OMe i-Pr 0 CF₃ 2-53 OCH₂CH₂OMe Me1 CF₃ 2-54 OCH₂CH₂OMe Et 1 CF₃ 2-55 OCH₂CH₂OMe n-Pr 1 CF₃ 2-56OCH₂CH₂OMe i-Pr 1 CF₃ 2-57 OCH₂CH₂OMe Me 2 CF₃ 2-58 OCH₂CH₂OMe Et 2 CF₃2-59 OCH₂CH₂OMe n-Pr 2 CF₃ 2-60 OCH₂CH₂OMe i-Pr 2 CF₃ 2-61 OCH₂CH₂SMe Me0 CF₃ 2-62 OCH₂CH₂SMe Et 0 CF₃ 2-63 OCH₂CH₂SMe n-Pr 0 CF₃ 2-64OCH₂CH₂SMe i-Pr 0 CF₃ 2-65 OCH₂CH₂SMe Me 1 CF₃ 2-66 OCH₂CH₂SMe Et 1 CF₃2-67 OCH₂CH₂SMe n-Pr 1 CF₃ 2-68 OCH₂CH₂SMe i-Pr 1 CF₃ 2-69 OCH₂CH₂SMe Me2 CF₃ 2-70 OCH₂CH₂SMe Et 2 CF₃ 2-71 OCH₂CH₂SMe n-Pr 2 CF₃ 2-72OCH₂CH₂SMe i-Pr 2 CF₃ 2-73 OCH₂CH₂SO₂Me Me 0 CF₃ 2-74 OCH₂CH₂SO₂Me Et 0CF₃ 2-75 OCH₂CH₂SO₂Me n-Pr 0 CF₃ 2-76 OCH₂CH₂SO₂Me i-Pr 0 CF₃ 2-77OCH₂CH₂SO₂Me Me 1 CF₃ 2-78 OCH₂CH₂SO₂Me Et 1 CF₃ 2-79 OCH₂CH₂SO₂Me n-Pr1 CF₃ 2-80 OCH₂CH₂SO₂Me i-Pr 1 CF₃ 2-81 OCH₂CH₂SO₂Me Me 2 CF₃ 2-82OCH₂CH₂SO₂Me Et 2 CF₃ 2-83 OCH₂CH₂SO₂Me n-Pr 2 CF₃ 2-84 OCH₂CH₂SO₂Mei-Pr 2 CF₃ 2-85 OCOMe Me 0 CF₃ 2-86 OCOMe Et 0 CF₃ 2-87 OCOMe n-Pr 0 CF₃2-88 OCOMe i-Pr 0 CF₃ 2-89 OCOMe Me 1 CF₃ 2-90 OCOMe Et 1 CF₃ 2-91 OCOMen-Pr 1 CF₃ 2-92 OCOMe i-Pr 1 CF₃ 2-93 OCOMe Me 2 CF₃ 2-94 OCOMe Et 2 CF₃2-95 OCOMe n-Pr 2 CF₃ 2-96 OCOMe i-Pr 2 CF₃ 2-97 OSO₂Me Me 0 CF₃ 2-98OSO₂Me Et 0 CF₃ 2-99 OSO₂Me n-Pr 0 CF₃ 2-100 OSO₂Me i-Pr 0 CF₃ 2-101OSO₂Me Me 1 CF₃ 2-102 OSO₂Me Et 1 CF₃ 2-103 OSO₂Me n-Pr 1 CF₃ 2-104OSO₂Me i-Pr 1 CF₃ 2-105 OSO₂Me Me 2 CF₃ 2-106 OSO₂Me Et 2 CF₃ 2-107OSO₂Me n-Pr 2 CF₃ 2-108 OSO₂Me i-Pr 2 CF₃ 2-109 OMe Me 0 C₂F₅ 2-110 OMeEt 0 C₂F₅ 2-111 OMe n-Pr 0 C₂F₅ 2-112 OMe i-Pr 0 C₂F₅ 2-113 OMe Me 1C₂F₅ 2-114 OMe Et 1 C₂F₅ 2-115 OMe n-Pr 1 C₂F₅ 2-116 OMe i-Pr 1 C₂F₅2-117 OMe Me 2 C₂F₅ 2-118 OMe Et 2 C₂F₅ 2-119 OMe n-Pr 2 C₂F₅ 2-120 OMei-Pr 2 C₂F₅ 2-121 OEt Me 0 C₂F₅ 2-122 OEt Et 0 C₂F₅ 2-123 OEt n-Pr 0C₂F₅ 2-124 OEt i-Pr 0 C₂F₅ 2-125 OEt Me 1 C₂F₅ 2-126 OEt Et 1 C₂F₅ 2-127OEt n-Pr 1 C₂F₅ 2-128 OEt i-Pr 1 C₂F₅ 2-129 OEt Me 2 C₂F₅ 2-130 OEt Et 2C₂F₅ 2-131 OEt n-Pr 2 C₂F₅ 2-132 OEt i-Pr 2 C₂F₅ 2-133 O—CH₂—c-Pr Me 0C₂F₅ 2-134 O—CH₂—c-Pr Et 0 C₂F₅ 2-135 O—CH₂—c-Pr n-Pr 0 C₂F₅ 2-136O—CH₂—c-Pr i-Pr 0 C₂F₅ 2-137 O—CH₂—c-Pr Me 1 C₂F₅ 2-138 O—CH₂—c-Pr Et 1C₂F₅ 2-139 O—CH₂—c-Pr n-Pr 1 C₂F₅ 2-140 O—CH₂—c-Pr i-Pr 1 C₂F₅ 2-141O—CH₂—c-Pr Me 2 C₂F₅ 2-142 O—CH₂—c-Pr Et 2 C₂F₅ 2-143 O—CH₂—c-Pr n-Pr 2C₂F₅ 2-144 O—CH₂—c-Pr i-Pr 2 C₂F₅ 2-145 OCH₂CH₂OMe Me 0 C₂F₅ 2-146OCH₂CH₂OMe Et 0 C₂F₅ 2-147 OCH₂CH₂OMe n-Pr 0 C₂F₅ 2-148 OCH₂CH₂OMe i-Pr0 C₂F₅ 2-149 OCH₂CH₂OMe Me 1 C₂F₅ 2-150 OCH₂CH₂OMe Et 1 C₂F₅ 2-151OCH₂CH₂OMe n-Pr 1 C₂F₅ 2-152 OCH₂CH₂OMe i-Pr 1 C₂F₅ 2-153 OCH₂CH₂OMe Me2 C₂F₅ 2-154 OCH₂CH₂OMe Et 2 C₂F₅ 2-155 OCH₂CH₂OMe n-Pr 2 C₂F₅ 2-156OCH₂CH₂OMe i-Pr 2 C₂F₅ 2-157 OCH₂CH₂SMe Me 0 C₂F₅ 2-158 OCH₂CH₂SMe Et 0C₂F₅ 2-159 OCH₂CH₂SMe n-Pr 0 C₂F₅ 2-160 OCH₂CH₂SMe i-Pr 0 C₂F₅ 2-161OCH₂CH₂SMe Me 1 C₂F₅ 2-162 OCH₂CH₂SMe Et 1 C₂F₅ 2-163 OCH₂CH₂SMe n-Pr 1C₂F₅ 2-164 OCH₂CH₂SMe i-Pr 1 C₂F₅ 2-165 OCH₂CH₂SMe Me 2 C₂F₅ 2-166OCH₂CH₂SMe Et 2 C₂F₅ 2-167 OCH₂CH₂SMe n-Pr 2 C₂F₅ 2-168 OCH₂CH₂SMe i-Pr2 C₂F₅ 2-169 OCH₂CH₂SO₂Me Me 0 C₂F₅ 2-170 OCH₂CH₂SO₂Me Et 0 C₂F₅ 2-171OCH₂CH₂SO₂Me n-Pr 0 C₂F₅ 2-172 OCH₂CH₂SO₂Me i-Pr 0 C₂F₅ 2-173OCH₂CH₂SO₂Me Me 1 C₂F₅ 2-174 OCH₂CH₂SO₂Me Et 1 C₂F₅ 2-175 OCH₂CH₂SO₂Men-Pr 1 C₂F₅ 2-176 OCH₂CH₂SO₂Me i-Pr 1 C₂F₅ 2-177 OCH₂CH₂SO₂Me Me 2 C₂F₅2-178 OCH₂CH₂SO₂Me Et 2 C₂F₅ 2-179 OCH₂CH₂SO₂Me n-Pr 2 C₂F₅ 2-180OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 2-181 OMe Me 0 CCl₃ 2-182 OMe Et 0 CCl₃ 2-183OMe n-Pr 0 CCl₃ 2-184 OMe i-Pr 0 CCl₃ 2-185 OMe Me 1 CCl₃ 2-186 OMe Et 1CCl₃ 2-187 OMe n-Pr 1 CCl₃ 2-188 OMe i-Pr 1 CCl₃ 2-189 OMe Me 2 CCl₃2-190 OMe Et 2 CCl₃ 2-191 OMe n-Pr 2 CCl₃ 2-192 OMe i-Pr 2 CCl₃ 2-193OEt Me 0 CCl₃ 2-194 OEt Et 0 CCl₃ 2-195 OEt n-Pr 0 CCl₃ 2-196 OEt i-Pr 0CCl₃ 2-197 OEt Me 1 CCl₃ 2-198 OEt Et 1 CCl₃ 2-199 OEt n-Pr 1 CCl₃ 2-200OEt i-Pr 1 CCl₃ 2-201 OEt Me 2 CCl₃ 2-202 OEt Et 2 CCl₃ 2-203 OEt n-Pr 2CCl₃ 2-204 OEt i-Pr 2 CCl₃ 2-205 O—CH₂—c-Pr Me 0 CCl₃ 2-206 O—CH₂—c-PrEt 0 CCl₃ 2-207 O—CH₂—c-Pr n-Pr 0 CCl₃ 2-208 O—CH₂—c-Pr i-Pr 0 CCl₃2-209 O—CH₂—c-Pr Me 1 CCl₃ 2-210 O—CH₂—c-Pr Et 1 CCl₃ 2-211 O—CH₂—c-Prn-Pr 1 CCl₃ 2-212 O—CH₂—c-Pr i-Pr 1 CCl₃ 2-213 O—CH₂—c-Pr Me 2 CCl₃2-214 O—CH₂—c-Pr Et 2 CCl₃ 2-215 O—CH₂—c-Pr n-Pr 2 CCl₃ 2-216 O—CH₂—c-Pri-Pr 2 CCl₃ 2-217 OCH₂CH₂OMe Me 0 CCl₃ 2-218 OCH₂CH₂OMe Et 0 CCl₃ 2-219OCH₂CH₂OMe n-Pr 0 CCl₃ 2-220 OCH₂CH₂OMe i-Pr 0 CCl₃ 2-221 OCH₂CH₂OMe Me1 CCl₃ 2-222 OCH₂CH₂OMe Et 1 CCl₃ 2-223 OCH₂CH₂OMe n-Pr 1 CCl₃ 2-224OCH₂CH₂OMe i-Pr 1 CCl₃ 2-225 OCH₂CH₂OMe Me 2 CCl₃ 2-226 OCH₂CH₂OMe Et 2CCl₃ 2-227 OCH₂CH₂OMe n-Pr 2 CCl₃ 2-228 OCH₂CH₂OMe i-Pr 2 CCl₃ 2-229OCH₂CH₂SMe Me 0 CCl₃ 2-230 OCH₂CH₂SMe Et 0 CCl₃ 2-231 OCH₂CH₂SMe n-Pr 0CCl₃ 2-232 OCH2CH2SMe i-Pr 0 CCl₃ 2-233 OCH₂CH₂SMe Me 1 CCl₃ 2-234OCH₂CH₂SMe Et 1 CCl₃ 2-235 OCH₂CH₂SMe n-Pr 1 CCl₃ 2-236 OCH₂CH₂SMe i-Pr1 CCl₃ 2-237 OCH₂CH₂SMe Me 2 CCl₃ 2-238 OCH₂CH₂SMe Et 2 CCl₃ 2-239OCH₂CH₂SMe n-Pr 2 CCl₃ 2-240 OCH₂CH₂SMe i-Pr 2 CCl₃ 2-241 OCH₂CH₂SO₂MeMe 0 CCl₃ 2-242 OCH₂CH₂SO₂Me Et 0 CCl₃ 2-243 OCH₂CH₂SO₂Me n-Pr 0 CCl₃2-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃ 2-245 OCH₂CH₂SO₂Me Me 1 CCl₃ 2-246OCH₂CH₂SO₂Me Et 1 CCl₃ 2-247 OCH₂CH₂SO₂Me n-Pr 1 CCl₃ 2-248 OCH₂CH₂SO₂Mei-Pr 1 CCl₃ 2-249 OCH₂CH₂SO₂Me Me 2 CCl₃ 2-250 OCH₂CH₂SO₂Me Et 2 CCl₃2-251 OCH₂CH₂SO₂Me n-Pr 2 CCl₃ 2-252 OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 2-253 OMeMe 0 CHF2 2-254 OMe Et 0 CHF2 2-255 OMe n-Pr 0 CHF2 2-256 OMe i-Pr 0CHF2 2-257 OMe Me 1 CHF2 2-258 OMe Et 1 CHF2 2-259 OMe n-Pr 1 CHF2 2-260OMe i-Pr 1 CHF2 2-261 OMe Me 2 CHF2 2-262 OMe Et 2 CHF2 2-263 OMe n-Pr 2CHF2 2-264 OMe i-Pr 2 CHF2 2-265 OEt Me 0 CHF2 2-266 OEt Et 0 CHF2 2-267OEt n-Pr 0 CHF2 2-268 OEt i-Pr 0 CHF2 2-269 OEt Me 1 CHF2 2-270 OEt Et 1CHF2 2-271 OEt n-Pr 1 CHF2 2-272 OEt i-Pr 1 CHF2 2-273 OEt Me 2 CHF22-274 OEt Et 2 CHF2 2-275 OEt n-Pr 2 CHF2 2-276 OEt i-Pr 2 CHF2 2-277O—CH₂—c-Pr Me 0 CHF2 2-278 O—CH₂—c-Pr Et 0 CHF2 2-279 O—CH₂—c-Pr n-Pr 0CHF2 2-280 O—CH₂—c-Pr i-Pr 0 CHF2 2-281 O—CH₂—c-Pr Me 1 CHF2 2-282O—CH₂—c-Pr Et 1 CHF2 2-283 O—CH₂—c-Pr n-Pr 1 CHF2 2-284 O—CH₂—c-Pr i-Pr1 CHF2 2-285 O—CH₂—c-Pr Me 2 CHF2 2-286 O—CH₂—c-Pr Et 2 CHF2 2-287O—CH₂—c-Pr n-Pr 2 CHF2 2-288 O—CH₂—c-Pr i-Pr 2 CHF2 2-289 OCH₂CH₂OMe Me0 CHF2 2-290 OCH₂CH₂OMe Et 0 CHF2 2-291 OCH₂CH₂OMe n-Pr 0 CHF2 2-292OCH₂CH₂OMe i-Pr 0 CHF2 2-293 OCH₂CH₂OMe Me 1 CHF2 2-294 OCH₂CH₂OMe Et 1CHF2 2-295 OCH₂CH₂OMe n-Pr 1 CHF2 2-296 OCH₂CH₂OMe i-Pr 1 CHF2 2-297OCH₂CH₂OMe Me 2 CHF2 2-298 OCH₂CH₂OMe Et 2 CHF2 2-299 OCH₂CH₂OMe n-Pr 2CHF2 2-300 OCH₂CH₂OMe i-Pr 2 CHF2 2-301 OCH₂CH₂SMe Me 0 CHF2 2-302OCH₂CH₂SMe Et 0 CHF2 2-303 OCH₂CH₂SMe n-Pr 0 CHF2 2-304 OCH₂CH₂SMe i-Pr0 CHF2 2-305 OCH₂CH₂SMe Me 1 CHF2 2-306 OCH₂CH₂SMe Et 1 CHF2 2-307OCH₂CH₂SMe n-Pr 1 CHF2 2-308 OCH₂CH₂SMe i-Pr 1 CHF2 2-309 OCH₂CH₂SMe Me2 CHF2 2-310 OCH₂CH₂SMe Et 2 CHF2 2-311 OCH₂CH₂SMe n-Pr 2 CHF2 2-312OCH₂CH₂SMe i-Pr 2 CHF2 2-313 OCH₂CH₂SO₂Me Me 0 CHF2 2-314 OCH₂CH₂SO₂MeEt 0 CHF2 2-315 OCH₂CH₂SO₂Me n-Pr 0 CHF2 2-316 OCH₂CH₂SO₂Me i-Pr 0 CHF22-317 OCH₂CH₂SO₂Me Me 1 CHF2 2-318 OCH₂CH₂SO₂Me Et 1 CHF2 2-319OCH₂CH₂SO₂Me n-Pr 1 CHF2 2-320 OCH₂CH₂SO₂Me i-Pr 1 CHF2 2-321OCH₂CH₂SO₂Me Me 2 CHF2 2-322 OCH₂CH₂SO₂Me Et 2 CHF2 2-323 OCH₂CH₂SO₂Men-Pr 2 CHF2 2-324 OCH₂CH₂SO₂Me i-Pr 2 CHF2 2-325 OMe Me 0 CF(CF₃)₂ 2-326OMe Et 0 CF(CF₃)₂ 2-327 OMe n-Pr 0 CF(CF₃)₂ 2-328 OMe i-Pr 0 CF(CF₃)₂2-329 OMe Me 1 CF(CF₃)₂ 2-330 OMe Et 1 CF(CF₃)₂ 2-331 OMe n-Pr 1CF(CF₃)₂ 2-332 OMe i-Pr 1 CF(CF₃)₂ 2-333 OMe Me 2 CF(CF₃)₂ 2-334 OMe Et2 CF(CF₃)₂ 2-335 OMe n-Pr 2 CF(CF₃)₂ 2-336 OMe i-Pr 2 CF(CF₃)₂ 2-337 OEtMe 0 CF(CF₃)₂ 2-338 OEt Et 0 CF(CF₃)₂ 2-339 OEt n-Pr 0 CF(CF₃)₂ 2-340OEt i-Pr 0 CF(CF₃)₂ 2-341 OEt Me 1 CF(CF₃)₂ 2-342 OEt Et 1 CF(CF₃)₂2-343 OEt n-Pr 1 CF(CF₃)₂ 2-344 OEt i-Pr 1 CF(CF₃)₂ 2-345 OEt Me 2CF(CF₃)₂ 2-346 OEt Et 2 CF(CF₃)₂ 2-347 OEt n-Pr 2 CF(CF₃)₂ 2-348 OEti-Pr 2 CF(CF₃)₂ 2-349 O—CH₂—c-Pr Me 0 CF(CF₃)₂ 2-350 O—CH₂—c-Pr Et 0CF(CF₃)₂ 2-351 O—CH₂—c-Pr n-Pr 0 CF(CF₃)₂ 2-352 O—CH₂—c-Pr i-Pr 0CF(CF₃)₂ 2-353 O—CH₂—c-Pr Me 1 CF(CF₃)₂ 2-354 O—CH₂—c-Pr Et 1 CF(CF₃)₂2-355 O—CH₂—c-Pr n-Pr 1 CF(CF₃)₂ 2-356 O—CH₂—c-Pr i-Pr 1 CF(CF₃)₂ 2-357O—CH₂—c-Pr Me 2 CF(CF₃)₂ 2-358 O—CH₂—c-Pr Et 2 CF(CF₃)₂ 2-359 O—CH₂—c-Prn-Pr 2 CF(CF₃)₂ 2-360 O—CH₂—c-Pr i-Pr 2 CF(CF₃)₂ 2-361 OCH₂CH₂OMe Me 0CF(CF₃)₂ 2-362 OCH₂CH₂OMe Et 0 CF(CF₃)₂ 2-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂2-364 OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 2-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 2-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 2-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 2-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 2-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 2-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 2-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 2-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 2-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 2-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 2-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 2-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 2-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 2-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 2-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 2-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 2-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 2-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 2-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 2-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 2-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 2-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 2-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 2-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 2-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 2-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 2-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 2-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 2-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 2-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 2-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 2-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

TABLE 3 Compounds of the formula (I) according to the invention in whichR² is hydroxyl, R³, R⁴, R⁷ and R⁸ are each hydrogen and R⁵ and R⁶ areeach methyl. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 3-1  OH Me 0 CF₃ 3-2  OHEt 0 CF₃ 3-3  OH n-Pr 0 CF₃ 3-4  OH i-Pr 0 CF₃ 3-5  OH Me 1 CF₃ 3-6  OHEt 1 CF₃ 3-7  OH n-Pr 1 CF₃ 3-8  OH i-Pr 1 CF₃ 3-9  OH Me 2 CF₃ 3-10  OHEt 2 CF₃ 3-11  OH n-Pr 2 CF₃ 3-12  OH i-Pr 2 CF₃ 3-13  OMe Me 0 CF₃3-14  OMe Et 0 CF₃ 3-15  OMe n-Pr 0 CF₃ 3-16  OMe i-Pr 0 CF₃ 3-17  OMeMe 1 CF₃ 16.71 (s, 1H), 7.57 (d, 1H), 7.42 (d, 1H), 3.87 (s, 3H), 3.07(s, 3H), 2.71 (d, 1H), 2.64 (d, 1H), 2.38 (d, 1H), 2.24 (d, 1H), 1.17(s, 3H), 1.11 (s, 3H) 3-18  OMe Et 1 CF₃ 3-19  OMe n-Pr 1 CF₃ 3-20  OMei-Pr 1 CF₃ 3-21  OMe Me 2 CF₃ 3-22  OMe Et 2 CF₃ 3-23  OMe n-Pr 2 CF₃3-24  OMe i-Pr 2 CF₃ 3-25  OEt Me 0 CF₃ 3-26  OEt Et 0 CF₃ 3-27  OEtn-Pr 0 CF₃ 3-28  OEt i-Pr 0 CF₃ 3-29  OEt Me 1 CF₃ 3-30  OEt Et 1 CF₃3-31  OEt n-Pr 1 CF₃ 3-32  OEt i-Pr 1 CF₃ 3-33  OEt Me 2 CF₃ 3-34  OEtEt 2 CF₃ 3-35  OEt n-Pr 2 CF₃ 3-36  OEt i-Pr 2 CF₃ 3-37  O—CH₂₋c-Pr Me 0CF₃ 3-38  O—CH₂₋c-Pr Et 0 CF₃ 3-39  O—CH₂₋c-Pr n-Pr 0 CF₃ 3-40 O—CH₂₋c-Pr i-Pr 0 CF₃ 3-41  O—CH₂₋c-Pr Me 1 CF₃ 3-42  O—CH₂₋c-Pr Et 1CF₃ 3-43  O—CH₂₋c-Pr n-Pr 1 CF₃ 3-44  O—CH₂₋c-Pr i-Pr 1 CF₃ 3-45 O—CH₂₋c-Pr Me 2 CF₃ 3-46  O—CH₂₋c-Pr Et 2 CF₃ 3-47  O—CH₂₋c-Pr n-Pr 2CF₃ 3-48  O—CH₂₋c-Pr i-Pr 2 CF₃ 3-49  OCH₂CH₂OMe Me 0 CF₃ 3-50 OCH₂CH₂OMe Et 0 CF₃ 3-51  OCH₂CH₂OMe n-Pr 0 CF₃ 3-52  OCH₂CH₂OMe i-Pr 0CF₃ 3-53  OCH₂CH₂OMe Me 1 CF₃ 3-54  OCH₂CH₂OMe Et 1 CF₃ 3-55  OCH₂CH₂OMen-Pr 1 CF₃ 3-56  OCH₂CH₂OMe i-Pr 1 CF₃ 3-57  OCH₂CH₂OMe Me 2 CF₃ 3-58 OCH₂CH₂OMe Et 2 CF₃ 3-59  OCH₂CH₂OMe n-Pr 2 CF₃ 3-60  OCH₂CH₂OMe i-Pr 2CF₃ 3-61  OCH₂CH₂SMe Me 0 CF₃ 3-62  OCH₂CH₂SMe Et 0 CF₃ 3-63  OCH₂CH₂SMen-Pr 0 CF₃ 3-64  OCH₂CH₂SMe i-Pr 0 CF₃ 3-65  OCH₂CH₂SMe Me 1 CF₃ 3-66 OCH₂CH₂SMe Et 1 CF₃ 3-67  OCH₂CH₂SMe n-Pr 1 CF₃ 3-68  OCH₂CH₂SMe i-Pr 1CF₃ 3-69  OCH₂CH₂SMe Me 2 CF₃ 3-70  OCH₂CH₂SMe Et 2 CF₃ 3-71  OCH₂CH₂SMen-Pr 2 CF₃ 3-72  OCH₂CH₂SMe i-Pr 2 CF₃ 3-73  OCH₂CH₂SO₂Me Me 0 CF₃ 3-74 OCH₂CH₂SO₂Me Et 0 CF₃ 3-75  OCH₂CH₂SO₂Me n-Pr 0 CF₃ 3-76  OCH₂CH₂SO₂Mei-Pr 0 CF₃ 3-77  OCH₂CH₂SO₂Me Me 1 CF₃ 3-78  OCH₂CH₂SO₂Me Et 1 CF₃ 3-79 OCH₂CH₂SO₂Me n-Pr 1 CF₃ 3-80  OCH₂CH₂SO₂Me i-Pr 1 CF₃ 3-81  OCH₂CH₂SO₂MeMe 2 CF₃ 3-82  OCH₂CH₂SO₂Me Et 2 CF₃ 3-83  OCH₂CH₂SO₂Me n-Pr 2 CF₃ 3-84 OCH₂CH₂SO₂Me i-Pr 2 CF₃ 3-85  OCOMe Me 0 CF₃ 3-86  OCOMe Et 0 CF₃ 3-87 OCOMe n-Pr 0 CF₃ 3-88  OCOMe i-Pr 0 CF₃ 3-89  OCOMe Me 1 CF₃ 3-90  OCOMeEt 1 CF₃ 3-91  OCOMe n-Pr 1 CF₃ 3-92  OCOMe i-Pr 1 CF₃ 3-93  OCOMe Me 2CF₃ 3-94  OCOMe Et 2 CF₃ 3-95  OCOMe n-Pr 2 CF₃ 3-96  OCOMe i-Pr 2 CF₃3-97  OSO₂Me Me 0 CF₃ 3-98  OSO₂Me Et 0 CF₃ 3-99  OSO₂Me n-Pr 0 CF₃3-100 OSO₂Me i-Pr 0 CF₃ 3-101 OSO₂Me Me 1 CF₃ 3-102 OSO₂Me Et 1 CF₃3-103 OSO₂Me n-Pr 1 CF₃ 3-104 OSO₂Me i-Pr 1 CF₃ 3-105 OSO₂Me Me 2 CF₃3-106 OSO₂Me Et 2 CF₃ 3-107 OSO₂Me n-Pr 2 CF₃ 3-108 OSO₂Me i-Pr 2 CF₃3-109 OMe Me 0 C₂F₅ 3-110 OMe Et 0 C₂F₅ 3-111 OMe n-Pr 0 C₂F₅ 3-112 OMei-Pr 0 C₂F₅ 3-113 OMe Me 1 C₂F₅ 3-114 OMe Et 1 C₂F₅ 3-115 OMe n-Pr 1C₂F₅ 3-116 OMe i-Pr 1 C₂F₅ 3-117 OMe Me 2 C₂F₅ 3-118 OMe Et 2 C₂F₅ 3-119OMe n-Pr 2 C₂F₅ 3-120 OMe i-Pr 2 C₂F₅ 3-121 OEt Me 0 C₂F₅ 3-122 OEt Et 0C₂F₅ 3-123 OEt n-Pr 0 C₂F₅ 3-124 OEt i-Pr 0 C₂F₅ 3-125 OEt Me 1 C₂F₅3-126 OEt Et 1 C₂F₅ 3-127 OEt n-Pr 1 C₂F₅ 3-128 OEt i-Pr 1 C₂F₅ 3-129OEt Me 2 C₂F₅ 3-130 OEt Et 2 C₂F₅ 3-131 OEt n-Pr 2 C₂F₅ 3-132 OEt i-Pr 2C₂F₅ 3-133 O—CH₂₋c-Pr Me 0 C₂F₅ 3-134 O—CH₂₋c-Pr Et 0 C₂F₅ 3-135O—CH₂₋c-Pr n-Pr 0 C₂F₅ 3-136 O—CH₂₋c-Pr i-Pr 0 C₂F₅ 3-137 O—CH₂₋c-Pr Me1 C₂F₅ 3-138 O—CH₂₋c-Pr Et 1 C₂F₅ 3-139 O—CH₂₋c-Pr n-Pr 1 C₂F₅ 3-140O—CH₂₋c-Pr i-Pr 1 C₂F₅ 3-141 O—CH₂₋c-Pr Me 2 C₂F₅ 3-142 O—CH₂₋c-Pr Et 2C₂F₅ 3-143 O—CH₂₋c-Pr n-Pr 2 C₂F₅ 3-144 O—CH₂₋c-Pr i-Pr 2 C₂F₅ 3-145OCH₂CH₂OMe Me 0 C₂F₅ 3-146 OCH₂CH₂OMe Et 0 C₂F₅ 3-147 OCH₂CH₂OMe n-Pr 0C₂F₅ 3-148 OCH₂CH₂OMe i-Pr 0 C₂F₅ 3-149 OCH₂CH₂OMe Me 1 C₂F₅ 3-150OCH₂CH₂OMe Et 1 C₂F₅ 3-151 OCH₂CH₂OMe n-Pr 1 C₂F₅ 3-152 OCH₂CH₂OMe i-Pr1 C₂F₅ 3-153 OCH₂CH₂OMe Me 2 C₂F₅ 3-154 OCH₂CH₂OMe Et 2 C₂F₅ 3-155OCH₂CH₂OMe n-Pr 2 C₂F₅ 3-156 OCH₂CH₂OMe i-Pr 2 C₂F₅ 3-157 OCH₂CH₂SMe Me0 C₂F₅ 3-158 OCH₂CH₂SMe Et 0 C₂F₅ 3-159 OCH₂CH₂SMe n-Pr 0 C₂F₅ 3-160OCH₂CH₂SMe i-Pr 0 C₂F₅ 3-161 OCH₂CH₂SMe Me 1 C₂F₅ 3-162 OCH₂CH₂SMe Et 1C₂F₅ 3-163 OCH₂CH₂SMe n-Pr 1 C₂F₅ 3-164 OCH₂CH₂SMe i-Pr 1 C₂F₅ 3-165OCH₂CH₂SMe Me 2 C₂F₅ 3-166 OCH₂CH₂SMe Et 2 C₂F₅ 3-167 OCH₂CH₂SMe n-Pr 2C₂F₅ 3-168 OCH₂CH₂SMe i-Pr 2 C₂F₅ 3-169 OCH₂CH₂SO₂Me Me 0 C₂F₅ 3-170OCH₂CH₂SO₂Me Et 0 C₂F₅ 3-171 OCH₂CH₂SO₂Me n-Pr 0 C₂F₅ 3-172 OCH₂CH₂SO₂Mei-Pr 0 C₂F₅ 3-173 OCH₂CH₂SO₂Me Me 1 C₂F₅ 3-174 OCH₂CH₂SO₂Me Et 1 C₂F₅3-175 OCH₂CH₂SO₂Me n-Pr 1 C₂F₅ 3-176 OCH₂CH₂SO₂Me i-Pr 1 C₂F₅ 3-177OCH₂CH₂SO₂Me Me 2 C₂F₅ 3-178 OCH₂CH₂SO₂Me Et 2 C₂F₅ 3-179 OCH₂CH₂SO₂Men-Pr 2 C₂F₅ 3-180 OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 3-181 OMe Me 0 CCl₃ 3-182 OMeEt 0 CCl₃ 3-183 OMe n-Pr 0 CCl₃ 3-184 OMe i-Pr 0 CCl₃ 3-185 OMe Me 1CCl₃ 3-186 OMe Et 1 CCl₃ 3-187 OMe n-Pr 1 CCl₃ 3-188 OMe i-Pr 1 CCl₃3-189 OMe Me 2 CCl₃ 3-190 OMe Et 2 CCl₃ 3-191 OMe n-Pr 2 CCl₃ 3-192 OMei-Pr 2 CCl₃ 3-193 OEt Me 0 CCl₃ 3-194 OEt Et 0 CCl₃ 3-195 OEt n-Pr 0CCl₃ 3-196 OEt i-Pr 0 CCl₃ 3-197 OEt Me 1 CCl₃ 3-198 OEt Et 1 CCl₃ 3-199OEt n-Pr 1 CCl₃ 3-200 OEt i-Pr 1 CCl₃ 3-201 OEt Me 2 CCl₃ 3-202 OEt Et 2CCl₃ 3-203 OEt n-Pr 2 CCl₃ 3-204 OEt i-Pr 2 CCl₃ 3-205 O—CH₂₋c-Pr Me 0CCl₃ 3-206 O—CH₂₋c-Pr Et 0 CCl₃ 3-207 O—CH₂₋c-Pr n-Pr 0 CCl₃ 3-208O—CH₂₋c-Pr i-Pr 0 CCl₃ 3-209 O—CH₂₋c-Pr Me 1 CCl₃ 3-210 O—CH₂₋c-Pr Et 1CCl₃ 3-211 O—CH₂₋c-Pr n-Pr 1 CCl₃ 3-212 O—CH₂₋c-Pr i-Pr 1 CCl₃ 3-213O—CH₂₋c-Pr Me 2 CCl₃ 3-214 O—CH₂₋c-Pr Et 2 CCl₃ 3-215 O—CH₂₋c-Pr n-Pr 2CCl₃ 3-216 O—CH₂₋c-Pr i-Pr 2 CCl₃ 3-217 OCH₂CH₂OMe Me 0 CCl₃ 3-218OCH₂CH₂OMe Et 0 CCl₃ 3-219 OCH₂CH₂OMe n-Pr 0 CCl₃ 3-220 OCH₂CH₂OMe i-Pr0 CCl₃ 3-221 OCH₂CH₂OMe Me 1 CCl₃ 3-222 OCH₂CH₂OMe Et 1 CCl₃ 3-223OCH₂CH₂OMe n-Pr 1 CCl₃ 3-224 OCH₂CH₂OMe i-Pr 1 CCl₃ 3-225 OCH₂CH₂OMe Me2 CCl₃ 3-226 OCH₂CH₂OMe Et 2 CCl₃ 3-227 OCH₂CH₂OMe n-Pr 2 CCl₃ 3-228OCH₂CH₂OMe i-Pr 2 CCl₃ 3-229 OCH₂CH₂SMe Me 0 CCl₃ 3-230 OCH₂CH₂SMe Et 0CCl₃ 3-231 OCH₂CH₂SMe n-Pr 0 CCl₃ 3-232 OCH₂CH₂SMe i-Pr 0 CCl₃ 3-233OCH₂CH₂SMe Me 1 CCl₃ 3-234 OCH₂CH₂SMe Et 1 CCl₃ 3-235 OCH₂CH₂SMe n-Pr 1CCl₃ 3-236 OCH₂CH₂SMe i-Pr 1 CCl₃ 3-237 OCH₂CH₂SMe Me 2 CCl₃ 3-238OCH₂CH₂SMe Et 2 CCl₃ 3-239 OCH₂CH₂SMe n-Pr 2 CCl₃ 3-240 OCH₂CH₂SMe i-Pr2 CCl₃ 3-241 OCH₂CH₂SO₂Me Me 0 CCl₃ 3-242 OCH₂CH₂SO₂Me Et 0 CCl₃ 3-243OCH₂CH₂SO₂Me n-Pr 0 CCl₃ 3-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃ 3-245OCH₂CH₂SO₂Me Me 1 CCl₃ 3-246 OCH₂CH₂SO₂Me Et 1 CCl₃ 3-247 OCH₂CH₂SO₂Men-Pr 1 CCl₃ 3-248 OCH₂CH₂SO₂Me i-Pr 1 CCl₃ 3-249 OCH₂CH₂SO₂Me Me 2 CCl₃3-250 OCH₂CH₂SO₂Me Et 2 CCl₃ 3-251 OCH₂CH₂SO₂Me n-Pr 2 CCl₃ 3-252OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 3-253 OMe Me 0 CHF₂ 3-254 OMe Et 0 CHF₂ 3-255OMe n-Pr 0 CHF₂ 3-256 OMe i-Pr 0 CHF₂ 3-257 OMe Me 1 CHF₂ 3-258 OMe Et 1CHF₂ 3-259 OMe n-Pr 1 CHF₂ 3-260 OMe i-Pr 1 CHF₂ 3-261 OMe Me 2 CHF₂3-262 OMe Et 2 CHF₂ 3-263 OMe n-Pr 2 CHF₂ 3-264 OMe i-Pr 2 CHF₂ 3-265OEt Me 0 CHF₂ 3-266 OEt Et 0 CHF₂ 3-267 OEt n-Pr 0 CHF₂ 3-268 OEt i-Pr 0CHF₂ 3-269 OEt Me 1 CHF₂ 3-270 OEt Et 1 CHF₂ 3-271 OEt n-Pr 1 CHF₂ 3-272OEt i-Pr 1 CHF₂ 3-273 OEt Me 2 CHF₂ 3-274 OEt Et 2 CHF₂ 3-275 OEt n-Pr 2CHF₂ 3-276 OEt i-Pr 2 CHF₂ 3-277 O—CH₂₋c-Pr Me 0 CHF₂ 3-278 O—CH₂₋c-PrEt 0 CHF₂ 3-279 O—CH₂₋c-Pr n-Pr 0 CHF₂ 3-280 O—CH₂₋c-Pr i-Pr 0 CHF₂3-281 O—CH₂₋c-Pr Me 1 CHF₂ 3-282 O—CH₂₋c-Pr Et 1 CHF₂ 3-283 O—CH₂₋c-Prn-Pr 1 CHF₂ 3-284 O—CH₂₋c-Pr i-Pr 1 CHF₂ 3-285 O—CH₂₋c-Pr Me 2 CHF₂3-286 O—CH₂₋c-Pr Et 2 CHF₂ 3-287 O—CH₂₋c-Pr n-Pr 2 CHF₂ 3-288 O—CH₂₋c-Pri-Pr 2 CHF₂ 3-289 OCH₂CH₂OMe Me 0 CHF₂ 3-290 OCH₂CH₂OMe Et 0 CHF₂ 3-291OCH₂CH₂OMe n-Pr 0 CHF₂ 3-292 OCH₂CH₂OMe i-Pr 0 CHF₂ 3-293 OCH₂CH₂OMe Me1 CHF₂ 3-294 OCH₂CH₂OMe Et 1 CHF₂ 3-295 OCH₂CH₂OMe n-Pr 1 CHF₂ 3-296OCH₂CH₂OMe i-Pr 1 CHF₂ 3-297 OCH₂CH₂OMe Me 2 CHF₂ 3-298 OCH₂CH₂OMe Et 2CHF₂ 3-299 OCH₂CH₂OMe n-Pr 2 CHF₂ 3-300 OCH₂CH₂OMe i-Pr 2 CHF₂ 3-301OCH₂CH₂SMe Me 0 CHF₂ 3-302 OCH₂CH₂SMe Et 0 CHF₂ 3-303 OCH₂CH₂SMe n-Pr 0CHF₂ 3-304 OCH₂CH₂SMe i-Pr 0 CHF₂ 3-305 OCH₂CH₂SMe Me 1 CHF₂ 3-306OCH₂CH₂SMe Et 1 CHF₂ 3-307 OCH₂CH₂SMe n-Pr 1 CHF₂ 3-308 OCH₂CH₂SMe i-Pr1 CHF₂ 3-309 OCH₂CH₂SMe Me 2 CHF₂ 3-310 OCH₂CH₂SMe Et 2 CHF₂ 3-311OCH₂CH₂SMe n-Pr 2 CHF₂ 3-312 OCH₂CH₂SMe i-Pr 2 CHF₂ 3-313 OCH₂CH₂SO₂MeMe 0 CHF₂ 3-314 OCH₂CH₂SO₂Me Et 0 CHF₂ 3-315 OCH₂CH₂SO₂Me n-Pr 0 CHF₂3-316 OCH₂CH₂SO₂Me i-Pr 0 CHF₂ 3-317 OCH₂CH₂SO₂Me Me 1 CHF₂ 3-318OCH₂CH₂SO₂Me Et 1 CHF₂ 3-319 OCH₂CH₂SO₂Me n-Pr 1 CHF₂ 3-320 OCH₂CH₂SO₂Mei-Pr 1 CHF₂ 3-321 OCH₂CH₂SO₂Me Me 2 CHF₂ 3-322 OCH₂CH₂SO₂Me Et 2 CHF₂3-323 OCH₂CH₂SO₂Me n-Pr 2 CHF₂ 3-324 OCH₂CH₂SO₂Me i-Pr 2 CHF₂ 3-325 OMeMe 0 CF(CF₃)₂ 3-326 OMe Et 0 CF(CF₃)₂ 3-327 OMe n-Pr 0 CF(CF₃)₂ 3-328OMe i-Pr 0 CF(CF₃)₂ 3-329 OMe Me 1 CF(CF₃)₂ 3-330 OMe Et 1 CF(CF₃)₂3-331 OMe n-Pr 1 CF(CF₃)₂ 3-332 OMe i-Pr 1 CF(CF₃)₂ 3-333 OMe Me 2CF(CF₃)₂ 3-334 OMe Et 2 CF(CF₃)₂ 3-335 OMe n-Pr 2 CF(CF₃)₂ 3-336 OMei-Pr 2 CF(CF₃)₂ 3-337 OEt Me 0 CF(CF₃)₂ 3-338 OEt Et 0 CF(CF₃)₂ 3-339OEt n-Pr 0 CF(CF₃)₂ 3-340 OEt i-Pr 0 CF(CF₃)₂ 3-341 OEt Me 1 CF(CF₃)₂3-342 OEt Et 1 CF(CF₃)₂ 3-343 OEt n-Pr 1 CF(CF₃)₂ 3-344 OEt i-Pr 1CF(CF₃)₂ 3-345 OEt Me 2 CF(CF₃)₂ 3-346 OEt Et 2 CF(CF₃)₂ 3-347 OEt n-Pr2 CF(CF₃)₂ 3-348 OEt i-Pr 2 CF(CF₃)₂ 3-349 O—CH₂₋c-Pr Me 0 CF(CF₃)₂3-350 O—CH₂₋c-Pr Et 0 CF(CF₃)₂ 3-351 O—CH₂₋c-Pr n-Pr 0 CF(CF₃)₂ 3-352O—CH₂₋c-Pr i-Pr 0 CF(CF₃)₂ 3-353 O—CH₂₋c-Pr Me 1 CF(CF₃)₂ 3-354O—CH₂₋c-Pr Et 1 CF(CF₃)₂ 3-355 O—CH₂₋c-Pr n-Pr 1 CF(CF₃)₂ 3-356O—CH₂₋c-Pr i-Pr 1 CF(CF₃)₂ 3-357 O—CH₂₋c-Pr Me 2 CF(CF₃)₂ 3-358O—CH₂₋c-Pr Et 2 CF(CF₃)₂ 3-359 O—CH₂₋c-Pr n-Pr 2 CF(CF₃)₂ 3-360O—CH₂₋c-Pr i-Pr 2 CF(CF₃)₂ 3-361 OCH₂CH₂OMe Me 0 CF(CF₃)₂ 3-362OCH₂CH₂OMe Et 0 CF(CF₃)₂ 3-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂ 3-364OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 3-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 3-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 3-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 3-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 3-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 3-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 3-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 3-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 3-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 3-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 3-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 3-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 3-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 3-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 3-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 3-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 3-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 3-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 3-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 3-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 3-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 3-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 3-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 3-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 3-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 3-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 3-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 3-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 3-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 3-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 3-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 3-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

TABLE 4 Compounds of the formula (I) according to the invention in whichR² is hydroxyl, R³, R⁴,R⁵, R⁷ and R⁸ are each hydrogen and R⁶ is methyl.(I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 4-1  OH Me 0 CF₃ 4-2  OHEt 0 CF₃ 4-3  OH n-Pr 0 CF₃ 4-4  OH i-Pr 0 CF₃ 4-5  OH Me 1 CF₃ 4-6  OHEt 1 CF₃ 4-7  OH n-Pr 1 CF₃ 4-8  OH i-Pr 1 CF₃ 4-9  OH Me 2 CF₃ 4-10  OHEt 2 CF₃ 4-11  OH n-Pr 2 CF₃ 4-12  OH i-Pr 2 CF₃ 4-13  OMe Me 0 CF₃16.88 (s, 1H), 7.48 (d, 1H), 7.17 (d, 1H), 3.83 (s, 3H), 2.81 (m, 1H),2.53-2.45 (m, 2H), 2.42 (s, 3H), 2.31 (m, 1H), 2.13 (dd, 1H), 1.13 (d,3H) 4-14  OMe Et 0 CF₃ 4-15  OMe n-Pr 0 CF₃ 4-16  OMe i-Pr 0 CF₃ 4-17 OMe Me 1 CF₃ 16.68/16.57 (s, 1H), 7.54 (d, 1H), 7.41 (d/d, 1H), 3.86(s/s, 3H), 3.06 (s/s, 3H), 2.84 (m, 1H), 2.60-2.04 (m, 4H), 1.13 (m, 3H)4-18  OMe Et 1 CF₃ 4-19  OMe n-Pr 1 CF₃ 4-20  OMe i-Pr 1 CF₃ 4-21  OMeMe 2 CF₃ 16.61 (s, 1H), 7.71 (d, 1H), 7.50 (d, 1H), 3.83 (s, 3H), 3.30(s, 3H), 2.85 (m, 1H), 2.56-2.46 (m, 2H), 2.32 (m, 1H), 2.15 (dd, 1H),1.13 (d, 3H) 4-22  OMe Et 2 CF₃ 4-23  OMe n-Pr 2 CF₃ 4-24  OMe i-Pr 2CF₃ 4-25  OEt Me 0 CF₃ 4-26  OEt Et 0 CF₃ 4-27  OEt n-Pr 0 CF₃ 4-28  OEti-Pr 0 CF₃ 4-29  OEt Me 1 CF₃ 4-30  OEt Et 1 CF₃ 4-31  OEt n-Pr 1 CF₃4-32  OEt i-Pr 1 CF₃ 4-33  OEt Me 2 CF₃ 4-34  OEt Et 2 CF₃ 4-35  OEtn-Pr 2 CF₃ 4-36  OEt i-Pr 2 CF₃ 4-37  OCH₂-c-Pr Me 0 CF₃ 4-38  OCH₂-c-PrEt 0 CF₃ 4-39  OCH₂-c-Pr n-Pr 0 CF₃ 4-40  OCH₂-c-Pr i-Pr 0 CF₃ 4-41 OCH₂-c-Pr Me 1 CF₃ 4-42  OCH₂-c-Pr Et 1 CF₃ 4-43  OCH₂-c-Pr n-Pr 1 CF₃4-44  OCH₂-c-Pr i-Pr 1 CF₃ 4-45  OCH₂-c-Pr Me 2 CF₃ 4-46  OCH₂-c-Pr Et 2CF₃ 4-47  OCH₂-c-Pr n-Pr 2 CF₃ 4-48  OCH₂-c-Pr i-Pr 2 CF₃ 4-49 OCH₂CH₂OMe Me 0 CF₃ 4-50  OCH₂CH₂OMe Et 0 CF₃ 4-51  OCH₂CH₂OMe n-Pr 0CF₃ 4-52  OCH₂CH₂OMe i-Pr 0 CF₃ 4-53  OCH₂CH₂OMe Me 1 CF₃ 4-54 OCH₂CH₂OMe Et 1 CF₃ 4-55  OCH₂CH₂OMe n-Pr 1 CF₃ 4-56  OCH₂CH₂OMe i-Pr 1CF₃ 4-57  OCH₂CH₂OMe Me 2 CF₃ 4-58  OCH₂CH₂OMe Et 2 CF₃ 4-59  OCH₂CH₂OMen-Pr 2 CF₃ 4-60  OCH₂CH₂OMe i-Pr 2 CF₃ 4-61  OCH₂CH₂SMe Me 0 CF₃ 4-62 OCH₂CH₂SMe Et 0 CF₃ 4-63  OCH₂CH₂SMe n-Pr 0 CF₃ 4-64  OCH₂CH₂SMe i-Pr 0CF₃ 4-65  OCH₂CH₂SMe Me 1 CF₃ 4-66  OCH₂CH₂SMe Et 1 CF₃ 4-67  OCH₂CH₂SMen-Pr 1 CF₃ 4-68  OCH₂CH₂SMe i-Pr 1 CF₃ 4-69  OCH₂CH₂SMe Me 2 CF₃ 4-70 OCH₂CH₂SMe Et 2 CF₃ 4-71  OCH₂CH₂SMe n-Pr 2 CF₃ 4-72  OCH₂CH₂SMe i-Pr 2CF₃ 4-73  OCH₂CH₂SO₂Me Me 0 CF₃ 4-74  OCH₂CH₂SO₂Me Et 0 CF₃ 4-75 OCH₂CH₂SO₂Me n-Pr 0 CF₃ 4-76  OCH₂CH₂SO₂Me i-Pr 0 CF₃ 4-77  OCH₂CH₂SO₂MeMe 1 CF₃ 4-78  OCH₂CH₂SO₂Me Et 1 CF₃ 4-79  OCH₂CH₂SO₂Me n-Pr 1 CF₃ 4-80 OCH₂CH₂SO₂Me i-Pr 1 CF₃ 4-81  OCH₂CH₂SO₂Me Me 2 CF₃ 4-82  OCH₂CH₂SO₂MeEt 2 CF₃ 4-83  OCH₂CH₂SO₂Me n-Pr 2 CF₃ 4-84  OCH₂CH₂SO₂Me i-Pr 2 CF₃4-85  OCOMe Me 0 CF₃ 4-86  OCOMe Et 0 CF₃ 4-87  OCOMe n-Pr 0 CF₃ 4-88 OCOMe i-Pr 0 CF₃ 4-89  OCOMe Me 1 CF₃ 4-90  OCOMe Et 1 CF₃ 4-91  OCOMen-Pr 1 CF₃ 4-92  OCOMe i-Pr 1 CF₃ 4-93  OCOMe Me 2 CF₃ 4-94  OCOMe Et 2CF₃ 4-95  OCOMe n-Pr 2 CF₃ 4-96  OCOMe i-Pr 2 CF₃ 4-97  OSO₂Me Me 0 CF₃4-98  OSO₂Me Et 0 CF₃ 4-99  OSO₂Me n-Pr 0 CF₃ 4-100 OSO₂Me i-Pr 0 CF₃4-101 OSO₂Me Me 1 CF₃ 4-102 OSO₂Me Et 1 CF₃ 4-103 OSO₂Me n-Pr 1 CF₃4-104 OSO₂Me i-Pr 1 CF₃ 4-105 OSO₂Me Me 2 CF₃ 4-106 OSO₂Me Et 2 CF₃4-107 OSO₂Me n-Pr 2 CF₃ 4-108 OSO₂Me i-Pr 2 CF₃ 4-109 OMe Me 0 C₂F₅4-110 OMe Et 0 C₂F₅ 4-111 OMe n-Pr 0 C₂F₅ 4-112 OMe i-Pr 0 C₂F₅ 4-113OMe Me 1 C₂F₅ 4-114 OMe Et 1 C₂F₅ 4-115 OMe n-Pr 1 C₂F₅ 4-116 OMe i-Pr 1C₂F₅ 4-117 OMe Me 2 C₂F₅ 4-118 OMe Et 2 C₂F₅ 4-119 OMe n-Pr 2 C₂F₅ 4-120OMe i-Pr 2 C₂F₅ 4-121 OEt Me 0 C₂F₅ 4-122 OEt Et 0 C₂F₅ 4-123 OEt n-Pr 0C₂F₅ 4-124 OEt i-Pr 0 C₂F₅ 4-125 OEt Me 1 C₂F₅ 4-126 OEt Et 1 C₂F₅ 4-127OEt n-Pr 1 C₂F₅ 4-128 OEt i-Pr 1 C₂F₅ 4-129 OEt Me 2 C₂F₅ 4-130 OEt Et 2C₂F₅ 4-131 OEt n-Pr 2 C₂F₅ 4-132 OEt i-Pr 2 C₂F₅ 4-133 OCH₂-c-Pr Me 0C₂F₅ 4-134 OCH₂-c-Pr Et 0 C₂F₅ 4-135 OCH₂-c-Pr n-Pr 0 C₂F₅ 4-136OCH₂-c-Pr i-Pr 0 C₂F₅ 4-137 OCH₂-c-Pr Me 1 C₂F₅ 4-138 OCH₂-c-Pr Et 1C₂F₅ 4-139 OCH₂-c-Pr n-Pr 1 C₂F₅ 4-140 OCH₂-c-Pr i-Pr 1 C₂F₅ 4-141OCH₂-c-Pr Me 2 C₂F₅ 4-142 OCH₂-c-Pr Et 2 C₂F₅ 4-143 OCH₂-c-Pr n-Pr 2C₂F₅ 4-144 OCH₂-c-Pr i-Pr 2 C₂F₅ 4-145 OCH₂CH₂OMe Me 0 C₂F₅ 4-146OCH₂CH₂OMe Et 0 C₂F₅ 4-147 OCH₂CH₂OMe n-Pr 0 C₂F₅ 4-148 OCH₂CH₂OMe i-Pr0 C₂F₅ 4-149 OCH₂CH₂OMe Me 1 C₂F₅ 4-150 OCH₂CH₂OMe Et 1 C₂F₅ 4-151OCH₂CH₂OMe n-Pr 1 C₂F₅ 4-152 OCH₂CH₂OMe i-Pr 1 C₂F₅ 4-153 OCH₂CH₂OMe Me2 C₂F₅ 4-154 OCH₂CH₂OMe Et 2 C₂F₅ 4-155 OCH₂CH₂OMe n-Pr 2 C₂F₅ 4-156OCH₂CH₂OMe i-Pr 2 C₂F₅ 4-157 OCH₂CH₂SMe Me 0 C₂F₅ 4-158 OCH₂CH₂SMe Et 0C₂F₅ 4-159 OCH₂CH₂SMe n-Pr 0 C₂F₅ 4-160 OCH₂CH₂SMe i-Pr 0 C₂F₅ 4-161OCH₂CH₂SMe Me 1 C₂F₅ 4-162 OCH₂CH₂SMe Et 1 C₂F₅ 4-163 OCH₂CH₂SMe n-Pr 1C₂F₅ 4-164 OCH₂CH₂SMe i-Pr 1 C₂F₅ 4-165 OCH₂CH₂SMe Me 2 C₂F₅ 4-166OCH₂CH₂SMe Et 2 C₂F₅ 4-167 OCH₂CH₂SMe n-Pr 2 C₂F₅ 4-168 OCH₂CH₂SMe i-Pr2 C₂F₅ 4-169 OCH₂CH₂SO₂Me Me 0 C₂F₅ 4-170 OCH₂CH₂SO₂Me Et 0 C₂F₅ 4-171OCH₂CH₂SO₂Me n-Pr 0 C₂F₅ 4-172 OCH₂CH₂SO₂Me i-Pr 0 C₂F₅ 4-173OCH₂CH₂SO₂Me Me 1 C₂F₅ 4-174 OCH₂CH₂SO₂Me Et 1 C₂F₅ 4-175 OCH₂CH₂SO₂Men-Pr 1 C₂F₅ 4-176 OCH₂CH₂SO₂Me i-Pr 1 C₂F₅ 4-177 OCH₂CH₂SO₂Me Me 2 C₂F₅4-178 OCH₂CH₂SO₂Me Et 2 C₂F₅ 4-179 OCH₂CH₂SO₂Me n-Pr 2 C₂F₅ 4-180OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 4-181 OMe Me 0 CCl₃ 4-182 OMe Et 0 CCl₃ 4-183OMe n-Pr 0 CCl₃ 4-184 OMe i-Pr 0 CCl₃ 4-185 OMe Me 1 CCl₃ 4-186 OMe Et 1CCl₃ 4-187 OMe n-Pr 1 CCl₃ 4-188 OMe i-Pr 1 CCl₃ 4-189 OMe Me 2 CCl₃4-190 OMe Et 2 CCl₃ 4-191 OMe n-Pr 2 CCl₃ 4-192 OMe i-Pr 2 CCl₃ 4-193OEt Me 0 CCl₃ 4-194 OEt Et 0 CCl₃ 4-195 OEt n-Pr 0 CCl₃ 4-196 OEt i-Pr 0CCl₃ 4-197 OEt Me 1 CCl₃ 4-198 OEt Et 1 CCl₃ 4-199 OEt n-Pr 1 CCl₃ 4-200OEt i-Pr 1 CCl₃ 4-201 OEt Me 2 CCl₃ 4-202 OEt Et 2 CCl₃ 4-203 OEt n-Pr 2CCl₃ 4-204 OEt i-Pr 2 CCl₃ 4-205 OCH₂-c-Pr Me 0 CCl₃ 4-206 OCH₂-c-Pr Et0 CCl₃ 4-207 OCH₂-c-Pr n-Pr 0 CCl₃ 4-208 OCH₂-c-Pr i-Pr 0 CCl₃ 4-209OCH₂-c-Pr Me 1 CCl₃ 4-210 OCH₂-c-Pr Et 1 CCl₃ 4-211 OCH₂-c-Pr n-Pr 1CCl₃ 4-212 OCH₂-c-Pr i-Pr 1 CCl₃ 4-213 OCH₂-c-Pr Me 2 CCl₃ 4-214OCH₂-c-Pr Et 2 CCl₃ 4-215 OCH₂-c-Pr n-Pr 2 CCl₃ 4-216 OCH₂-c-Pr i-Pr 2CCl₃ 4-217 OCH₂CH₂OMe Me 0 CCl₃ 4-218 OCH₂CH₂OMe Et 0 CCl₃ 4-219OCH₂CH₂OMe n-Pr 0 CCl₃ 4-220 OCH₂CH₂OMe i-Pr 0 CCl₃ 4-221 OCH₂CH₂OMe Me1 CCl₃ 4-222 OCH₂CH₂OMe Et 1 CCl₃ 4-223 OCH₂CH₂OMe n-Pr 1 CCl₃ 4-224OCH₂CH₂OMe i-Pr 1 CCl₃ 4-225 OCH₂CH₂OMe Me 2 CCl₃ 4-226 OCH₂CH₂OMe Et 2CCl₃ 4-227 OCH₂CH₂OMe n-Pr 2 CCl₃ 4-228 OCH₂CH₂OMe i-Pr 2 CCl₃ 4-229OCH₂CH₂SMe Me 0 CCl₃ 4-230 OCH₂CH₂SMe Et 0 CCl₃ 4-231 OCH₂CH₂SMe n-Pr 0CCl₃ 4-232 OCH₂CH₂SMe i-Pr 0 CCl₃ 4-233 OCH₂CH₂SMe Me 1 CCl₃ 4-234OCH₂CH₂SMe Et 1 CCl₃ 4-235 OCH₂CH₂SMe n-Pr 1 CCl₃ 4-236 OCH₂CH₂SMe i-Pr1 CCl₃ 4-237 OCH₂CH₂SMe Me 2 CCl₃ 4-238 OCH₂CH₂SMe Et 2 CCl₃ 4-239OCH₂CH₂SMe n-Pr 2 CCl₃ 4-240 OCH₂CH₂SMe i-Pr 2 CCl₃ 4-241 OCH₂CH₂SO₂MeMe 0 CCl₃ 4-242 OCH₂CH₂SO₂Me Et 0 CCl₃ 4-243 OCH₂CH₂SO₂Me n-Pr 0 CCl₃4-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃ 4-245 OCH₂CH₂SO₂Me Me 1 CCl₃ 4-246OCH₂CH₂SO₂Me Et 1 CCl₃ 4-247 OCH₂CH₂SO₂Me n-Pr 1 CCl₃ 4-248 OCH₂CH₂SO₂Mei-Pr 1 CCl₃ 4-249 OCH₂CH₂SO₂Me Me 2 CCl₃ 4-250 OCH₂CH₂SO₂Me Et 2 CCl₃4-251 OCH₂CH₂SO₂Me n-Pr 2 CCl₃ 4-252 OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 4-253 OMeMe 0 CHF₂ 4-254 OMe Et 0 CHF₂ 4-255 OMe n-Pr 0 CHF₂ 4-256 OMe i-Pr 0CHF₂ 4-257 OMe Me 1 CHF₂ 4-258 OMe Et 1 CHF₂ 4-259 OMe n-Pr 1 CHF₂ 4-260OMe i-Pr 1 CHF₂ 4-261 OMe Me 2 CHF₂ 4-262 OMe Et 2 CHF₂ 4-263 OMe n-Pr 2CHF₂ 4-264 OMe i-Pr 2 CHF₂ 4-265 OEt Me 0 CHF₂ 4-266 OEt Et 0 CHF₂ 4-267OEt n-Pr 0 CHF₂ 4-268 OEt i-Pr 0 CHF₂ 4-269 OEt Me 1 CHF₂ 4-270 OEt Et 1CHF₂ 4-271 OEt n-Pr 1 CHF₂ 4-272 OEt i-Pr 1 CHF₂ 4-273 OEt Me 2 CHF₂4-274 OEt Et 2 CHF₂ 4-275 OEt n-Pr 2 CHF₂ 4-276 OEt i-Pr 2 CHF₂ 4-277OCH₂-c-Pr Me 0 CHF₂ 4-278 OCH₂-c-Pr Et 0 CHF₂ 4-279 OCH₂-c-Pr n-Pr 0CHF₂ 4-280 OCH₂-c-Pr i-Pr 0 CHF₂ 4-281 OCH₂-c-Pr Me 1 CHF₂ 4-282OCH₂-c-Pr Et 1 CHF₂ 4-283 OCH₂-c-Pr n-Pr 1 CHF₂ 4-284 OCH₂-c-Pr i-Pr 1CHF₂ 4-285 OCH₂-c-Pr Me 2 CHF₂ 4-286 OCH₂-c-Pr Et 2 CHF₂ 4-287 OCH₂-c-Prn-Pr 2 CHF₂ 4-288 OCH₂-c-Pr i-Pr 2 CHF₂ 4-289 OCH₂CH₂OMe Me 0 CHF₂ 4-290OCH₂CH₂OMe Et 0 CHF₂ 4-291 OCH₂CH₂OMe n-Pr 0 CHF₂ 4-292 OCH₂CH₂OMe i-Pr0 CHF₂ 4-293 OCH₂CH₂OMe Me 1 CHF₂ 4-294 OCH₂CH₂OMe Et 1 CHF₂ 4-295OCH₂CH₂OMe n-Pr 1 CHF₂ 4-296 OCH₂CH₂OMe i-Pr 1 CHF₂ 4-297 OCH₂CH₂OMe Me2 CHF₂ 4-298 OCH₂CH₂OMe Et 2 CHF₂ 4-299 OCH₂CH₂OMe n-Pr 2 CHF₂ 4-300OCH₂CH₂OMe i-Pr 2 CHF₂ 4-301 OCH₂CH₂SMe Me 0 CHF₂ 4-302 OCH₂CH₂SMe Et 0CHF₂ 4-303 OCH₂CH₂SMe n-Pr 0 CHF₂ 4-304 OCH₂CH₂SMe i-Pr 0 CHF₂ 4-305OCH₂CH₂SMe Me 1 CHF₂ 4-306 OCH₂CH₂SMe Et 1 CHF₂ 4-307 OCH₂CH₂SMe n-Pr 1CHF₂ 4-308 OCH₂CH₂SMe i-Pr 1 CHF₂ 4-309 OCH₂CH₂SMe Me 2 CHF₂ 4-310OCH₂CH₂SMe Et 2 CHF₂ 4-311 OCH₂CH₂SMe n-Pr 2 CHF₂ 4-312 OCH₂CH₂SMe i-Pr2 CHF₂ 4-313 OCH₂CH₂SO₂Me Me 0 CHF₂ 4-314 OCH₂CH₂SO₂Me Et 0 CHF₂ 4-315OCH₂CH₂SO₂Me n-Pr 0 CHF₂ 4-316 OCH₂CH₂SO₂Me i-Pr 0 CHF₂ 4-317OCH₂CH₂SO₂Me Me 1 CHF₂ 4-318 OCH₂CH₂SO₂Me Et 1 CHF₂ 4-319 OCH₂CH₂SO₂Men-Pr 1 CHF₂ 4-320 OCH₂CH₂SO₂Me i-Pr 1 CHF₂ 4-321 OCH₂CH₂SO₂Me Me 2 CHF₂4-322 OCH₂CH₂SO₂Me Et 2 CHF₂ 4-323 OCH₂CH₂SO₂Me n-Pr 2 CHF₂ 4-324OCH₂CH₂SO₂Me i-Pr 2 CHF₂ 4-325 OMe Me 0 CF(CF₃)₂ 4-326 OMe Et 0 CF(CF₃)₂4-327 OMe n-Pr 0 CF(CF₃)₂ 4-328 OMe i-Pr 0 CF(CF₃)₂ 4-329 OMe Me 1CF(CF₃)₂ 4-330 OMe Et 1 CF(CF₃)₂ 4-331 OMe n-Pr 1 CF(CF₃)₂ 4-332 OMei-Pr 1 CF(CF₃)₂ 4-333 OMe Me 2 CF(CF₃)₂ 4-334 OMe Et 2 CF(CF₃)₂ 4-335OMe n-Pr 2 CF(CF₃)₂ 4-336 OMe i-Pr 2 CF(CF₃)₂ 4-337 OEt Me 0 CF(CF₃)₂4-338 OEt Et 0 CF(CF₃)₂ 4-339 OEt n-Pr 0 CF(CF₃)₂ 4-340 OEt i-Pr 0CF(CF₃)₂ 4-341 OEt Me 1 CF(CF₃)₂ 4-342 OEt Et 1 CF(CF₃)₂ 4-343 OEt n-Pr1 CF(CF₃)₂ 4-344 OEt i-Pr 1 CF(CF₃)₂ 4-345 OEt Me 2 CF(CF₃)₂ 4-346 OEtEt 2 CF(CF₃)₂ 4-347 OEt n-Pr 2 CF(CF₃)₂ 4-348 OEt i-Pr 2 CF(CF₃)₂ 4-349O—CH₂₋c-Pr Me 0 CF(CF₃)₂ 4-350 O—CH₂₋c-Pr Et 0 CF(CF₃)₂ 4-351 O—CH₂₋c-Prn-Pr 0 CF(CF₃)₂ 4-352 O—CH₂₋c-Pr i-Pr 0 CF(CF₃)₂ 4-353 O—CH₂₋c-Pr Me 1CF(CF₃)₂ 4-354 O—CH₂₋c-Pr Et 1 CF(CF₃)₂ 4-355 O—CH₂₋c-Pr n-Pr 1 CF(CF₃)₂4-356 O—CH₂₋c-Pr i-Pr 1 CF(CF₃)₂ 4-357 O—CH₂₋c-Pr Me 2 CF(CF₃)₂ 4-358O—CH₂₋c-Pr Et 2 CF(CF₃)₂ 4-359 O—CH₂₋c-Pr n-Pr 2 CF(CF₃)₂ 4-360O—CH₂₋c-Pr i-Pr 2 CF(CF₃)₂ 4-361 OCH₂CH₂OMe Me 0 CF(CF₃)₂ 4-362OCH₂CH₂OMe Et 0 CF(CF₃)₂ 4-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂ 4-364OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 4-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 4-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 4-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 4-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 4-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 4-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 4-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 4-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 4-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 4-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 4-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 4-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 4-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 4-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 4-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 4-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 4-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 4-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 4-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 4-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 4-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 4-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 4-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 4-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 4-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 4-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 4-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 4-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 4-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 4-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 4-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 4-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

TABLE 5 Compounds of the formula (I) according to the invention in whichR² is hydroxyl, R⁴, R⁵, R⁶ and R⁷are each hydrogen and R³ and R⁸together are an ethylene group. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 5-1 OH Me 0 CF₃ 5-2 OH Et0 CF₃ 5-3 OH n-Pr 0 CF₃ 5-4 OH i-Pr 0 CF₃ 5-5 OH Me 1 CF₃ 5-6 OH Et 1CF₃ 5-7 OH n-Pr 1 CF₃ 5-8 OH i-Pr 1 CF₃ 5-9 OH Me 2 CF₃ 5-10 OH Et 2 CF₃5-11 OH n-Pr 2 CF₃ 5-12 OH i-Pr 2 CF₃ 5-13 OMe Me 0 CF₃ 5-14 OMe Et 0CF₃ 5-15 OMe n-Pr 0 CF₃ 5-16 OMe i-Pr 0 CF₃ 5-17 OMe Me 1 CF₃ 16.68 (s,1H), 7.56 (m, 1H), 7.42 (d, 1H), 3.85/3.83 (s, 3H), 3.17 (m, 1H),3.09/3.07 (s, 3H), 2.92 (m, 1H), 2.32-1.62 (m, 6H) 5-18 OMe Et 1 CF₃5-19 OMe n-Pr 1 CF₃ 5-20 OMe i-Pr 1 CF₃ 5-21 OMe Me 2 CF₃ 16.68 (s, 1H),7.72 (d, 1H), 7.53 (d, 1H), 3.82 (s, 3H), 3.31 (s, 3H), 3.18 (m, 1H),2.91 (m, 1H), 2.32-2.12 (m, 3H), 2.03 (m, 1H), 1.81-1.71 (m, 2H) 5-22OMe Et 2 CF₃ 5-23 OMe n-Pr 2 CF₃ 5-24 OMe i-Pr 2 CF₃ 5-25 OEt Me 0 CF₃5-26 OEt Et 0 CF₃ 5-27 OEt n-Pr 0 CF₃ 5-28 OEt i-Pr 0 CF₃ 5-29 OEt Me 1CF₃ 5-30 OEt Et 1 CF₃ 5-31 OEt n-Pr 1 CF₃ 5-32 OEt i-Pr 1 CF₃ 5-33 OEtMe 2 CF₃ 5-34 OEt Et 2 CF₃ 5-35 OEt n-Pr 2 CF₃ 5-36 OEt i-Pr 2 CF₃ 5-37O—CH₂—c-Pr Me 0 CF₃ 5-38 O—CH₂—c-Pr Et 0 CF₃ 5-39 O—CH₂—c-Pr n-Pr 0 CF₃5-40 O—CH₂—c-Pr i-Pr 0 CF₃ 5-41 O—CH₂—c-Pr Me 1 CF₃ 5-42 O—CH₂—c-Pr Et 1CF₃ 5-43 O—CH₂—c-Pr n-Pr 1 CF₃ 5-44 O—CH₂—c-Pr i-Pr 1 CF₃ 5-45O—CH₂—c-Pr Me 2 CF₃ 5-46 O—CH₂—c-Pr Et 2 CF₃ 5-47 O—CH₂—c-Pr n-Pr 2 CF₃5-48 O—CH₂—c-Pr i-Pr 2 CF₃ 5-49 OCH₂CH₂OMe Me 0 CF₃ 5-50 OCH₂CH₂OMe Et 0CF₃ 5-51 OCH₂CH₂OMe n-Pr 0 CF₃ 5-52 OCH₂CH₂OMe i-Pr 0 CF₃ 5-53OCH₂CH₂OMe Me 1 CF₃ 5-54 OCH₂CH₂OMe Et 1 CF₃ 5-55 OCH₂CH₂OMe n-Pr 1 CF₃5-56 OCH₂CH₂OMe i-Pr 1 CF₃ 5-57 OCH₂CH₂OMe Me 2 CF₃ 5-58 OCH₂CH₂OMe Et 2CF₃ 5-59 OCH₂CH₂OMe n-Pr 2 CF₃ 5-60 OCH₂CH₂OMe i-Pr 2 CF₃ 5-61OCH₂CH₂SMe Me 0 CF₃ 5-62 OCH₂CH₂SMe Et 0 CF₃ 5-63 OCH₂CH₂SMe n-Pr 0 CF₃5-64 OCH₂CH₂SMe i-Pr 0 CF₃ 5-65 OCH₂CH₂SMe Me 1 CF₃ 5-66 OCH₂CH₂SMe Et 1CF₃ 5-67 OCH₂CH₂SMe n-Pr 1 CF₃ 5-68 OCH₂CH₂SMe i-Pr 1 CF₃ 5-69OCH₂CH₂SMe Me 2 CF₃ 5-70 OCH₂CH₂SMe Et 2 CF₃ 5-71 OCH₂CH₂SMe n-Pr 2 CF₃5-72 OCH₂CH₂SMe i-Pr 2 CF₃ 5-73 OCH₂CH₂SO₂Me Me 0 CF₃ 5-74 OCH₂CH₂SO₂MeEt 0 CF₃ 5-75 OCH₂CH₂SO₂Me n-Pr 0 CF₃ 5-76 OCH₂CH₂SO₂Me i-Pr 0 CF₃ 5-77OCH₂CH₂SO₂Me Me 1 CF₃ 5-78 OCH₂CH₂SO₂Me Et 1 CF₃ 5-79 OCH₂CH₂SO₂Me n-Pr1 CF₃ 5-80 OCH₂CH₂SO₂Me i-Pr 1 CF₃ 5-81 OCH₂CH₂SO₂Me Me 2 CF₃ 5-82OCH₂CH₂SO₂Me Et 2 CF₃ 5-83 OCH₂CH₂SO₂Me n-Pr 2 CF₃ 5-84 OCH₂CH₂SO₂Mei-Pr 2 CF₃ 5-85 OCOMe Me 0 CF₃ 5-86 OCOMe Et 0 CF₃ 5-87 OCOMe n-Pr 0 CF₃5-88 OCOMe i-Pr 0 CF₃ 5-89 OCOMe Me 1 CF₃ 5-90 OCOMe Et 1 CF₃ 5-91 OCOMen-Pr 1 CF₃ 5-92 OCOMe i-Pr 1 CF₃ 5-93 OCOMe Me 2 CF₃ 5-94 OCOMe Et 2 CF₃5-95 OCOMe n-Pr 2 CF₃ 5-96 OCOMe i-Pr 2 CF₃ 5-97 OSO₂Me Me 0 CF₃ 5-98OSO₂Me Et 0 CF₃ 5-99 OSO₂Me n-Pr 0 CF₃ 5-100 OSO₂Me i-Pr 0 CF₃ 5-101OSO₂Me Me 1 CF₃ 5-102 OSO₂Me Et 1 CF₃ 5-103 OSO₂Me n-Pr 1 CF₃ 5-104OSO₂Me i-Pr 1 CF₃ 5-105 OSO₂Me Me 2 CF₃ 5-106 OSO₂Me Et 2 CF₃ 5-107OSO₂Me n-Pr 2 CF₃ 5-108 OSO₂Me i-Pr 2 CF₃ 5-109 OMe Me 0 C₂F₅ 5-110 OMeEt 0 C₂F₅ 5-111 OMe n-Pr 0 C₂F₅ 5-112 OMe i-Pr 0 C₂F₅ 5-113 OMe Me 1C₂F₅ 5-114 OMe Et 1 C₂F₅ 5-115 OMe n-Pr 1 C₂F₅ 5-116 OMe i-Pr 1 C₂F₅5-117 OMe Me 2 C₂F₅ 5-118 OMe Et 2 C₂F₅ 5-119 OMe n-Pr 2 C₂F₅ 5-120 OMei-Pr 2 C₂F₅ 5-121 OEt Me 0 C₂F₅ 5-122 OEt Et 0 C₂F₅ 5-123 OEt n-Pr 0C₂F₅ 5-124 OEt i-Pr 0 C₂F₅ 5-125 OEt Me 1 C₂F₅ 5-126 OEt Et 1 C₂F₅ 5-127OEt n-Pr 1 C₂F₅ 5-128 OEt i-Pr 1 C₂F₅ 5-129 OEt Me 2 C₂F₅ 5-130 OEt Et 2C₂F₅ 5-131 OEt n-Pr 2 C₂F₅ 5-132 OEt i-Pr 2 C₂F₅ 5-133 OCH₂—c-Pr Me 0C₂F₅ 5-134 OCH₂—c-Pr Et 0 C₂F₅ 5-135 OCH₂—c-Pr n-Pr 0 C₂F₅ 5-136OCH₂—c-Pr i-Pr 0 C₂F₅ 5-137 OCH₂—c-Pr Me 1 C₂F₅ 5-138 OCH₂—c-Pr Et 1C₂F₅ 5-139 OCH₂—c-Pr n-Pr 1 C₂F₅ 5-140 OCH₂—c-Pr i-Pr 1 C₂F₅ 5-141OCH₂—c-Pr Me 2 C₂F₅ 5-142 OCH₂—c-Pr Et 2 C₂F₅ 5-143 OCH₂—c-Pr n-Pr 2C₂F₅ 5-144 OCH₂—c-Pr i-Pr 2 C₂F₅ 5-145 OCH₂CH₂OMe Me 0 C₂F₅ 5-146OCH₂CH₂OMe Et 0 C₂F₅ 5-147 OCH₂CH₂OMe n-Pr 0 C₂F₅ 5-148 OCH₂CH₂OMe i-Pr0 C₂F₅ 5-149 OCH₂CH₂OMe Me 1 C₂F₅ 5-150 OCH₂CH₂OMe Et 1 C₂F₅ 5-151OCH₂CH₂OMe n-Pr 1 C₂F₅ 5-152 OCH₂CH₂OMe i-Pr 1 C₂F₅ 5-153 OCH₂CH₂OMe Me2 C₂F₅ 5-154 OCH₂CH₂OMe Et 2 C₂F₅ 5-155 OCH₂CH₂OMe n-Pr 2 C₂F₅ 5-156OCH₂CH₂OMe i-Pr 2 C₂F₅ 5-157 OCH₂CH₂SMe Me 0 C₂F₅ 5-158 OCH₂CH₂SMe Et 0C₂F₅ 5-159 OCH₂CH₂SMe n-Pr 0 C₂F₅ 5-160 OCH₂CH₂SMe i-Pr 0 C₂F₅ 5-161OCH₂CH₂SMe Me 1 C₂F₅ 5-162 OCH₂CH₂SMe Et 1 C₂F₅ 5-163 OCH₂CH₂SMe n-Pr 1C₂F₅ 5-164 OCH₂CH₂SMe i-Pr 1 C₂F₅ 5-165 OCH₂CH₂SMe Me 2 C₂F₅ 5-166OCH₂CH₂SMe Et 2 C₂F₅ 5-167 OCH₂CH₂SMe n-Pr 2 C₂F₅ 5-168 OCH₂CH₂SMe i-Pr2 C₂F₅ 5-169 OCH₂CH₂SO₂Me Me 0 C₂F₅ 5-170 OCH₂CH₂SO₂Me Et 0 C₂F₅ 5-171OCH₂CH₂SO₂Me n-Pr 0 C₂F₅ 5-172 OCH₂CH₂SO₂Me i-Pr 0 C₂F₅ 5-173OCH₂CH₂SO₂Me Me 1 C₂F₅ 5-174 OCH₂CH₂SO₂Me Et 1 C₂F₅ 5-175 OCH₂CH₂SO₂Men-Pr 1 C₂F₅ 5-176 OCH₂CH₂SO₂Me i-Pr 1 C₂F₅ 5-177 OCH₂CH₂SO₂Me Me 2 C₂F₅5-178 OCH₂CH₂SO₂Me Et 2 C₂F₅ 5-179 OCH₂CH₂SO₂Me n-Pr 2 C₂F₅ 5-180OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 5-181 OMe Me 0 CCl₃ 5-182 OMe Et 0 CCl₃ 5-183OMe n-Pr 0 CCl₃ 5-184 OMe i-Pr 0 CCl₃ 5-185 OMe Me 1 CCl₃ 5-186 OMe Et 1CCl₃ 5-187 OMe n-Pr 1 CCl₃ 5-188 OMe i-Pr 1 CCl₃ 5-189 OMe Me 2 CCl₃5-190 OMe Et 2 CCl₃ 5-191 OMe n-Pr 2 CCl₃ 5-192 OMe i-Pr 2 CCl₃ 5-193OEt Me 0 CCl₃ 5-194 OEt Et 0 CCl₃ 5-195 OEt n-Pr 0 CCl₃ 5-196 OEt i-Pr 0CCl₃ 5-197 OEt Me 1 CCl₃ 5-198 OEt Et 1 CCl₃ 5-199 OEt n-Pr 1 CCl₃ 5-200OEt i-Pr 1 CCl₃ 5-201 OEt Me 2 CCl₃ 5-202 OEt Et 2 CCl₃ 5-203 OEt n-Pr 2CCl₃ 5-204 OEt i-Pr 2 CCl₃ 5-205 OCH₂—c-Pr Me 0 CCl₃ 5-206 OCH₂—c-Pr Et0 CCl₃ 5-207 OCH₂—c-Pr n-Pr 0 CCl₃ 5-208 OCH₂—c-Pr i-Pr 0 CCl₃ 5-209OCH₂—c-Pr Me 1 CCl₃ 5-210 OCH₂—c-Pr Et 1 CCl₃ 5-211 OCH₂—c-Pr n-Pr 1CCl₃ 5-212 OCH₂—c-Pr i-Pr 1 CCl₃ 5-213 OCH₂—c-Pr Me 2 CCl₃ 5-214OCH₂—c-Pr Et 2 CCl₃ 5-215 OCH₂—c-Pr n-Pr 2 CCl₃ 5-216 OCH₂—c-Pr i-Pr 2CCl₃ 5-217 OCH₂CH₂OMe Me 0 CCl₃ 5-218 OCH₂CH₂OMe Et 0 CCl₃ 5-219OCH₂CH₂OMe n-Pr 0 CCl₃ 5-220 OCH₂CH₂OMe i-Pr 0 CCl₃ 5-221 OCH₂CH₂OMe Me1 CCl₃ 5-222 OCH₂CH₂OMe Et 1 CCl₃ 5-223 OCH₂CH₂OMe n-Pr 1 CCl₃ 5-224OCH₂CH₂OMe i-Pr 1 CCl₃ 5-225 OCH₂CH₂OMe Me 2 CCl₃ 5-226 OCH₂CH₂OMe Et 2CCl₃ 5-227 OCH₂CH₂OMe n-Pr 2 CCl₃ 5-228 OCH₂CH₂OMe i-Pr 2 CCl₃ 5-229OCH₂CH₂SMe Me 0 CCl₃ 5-230 OCH₂CH₂SMe Et 0 CCl₃ 5-231 OCH₂CH₂SMe n-Pr 0CCl₃ 5-232 OCH₂CH₂SMe i-Pr 0 CCl₃ 5-233 OCH₂CH₂SMe Me 1 CCl₃ 5-234OCH₂CH₂SMe Et 1 CCl₃ 5-235 OCH₂CH₂SMe n-Pr 1 CCl₃ 5-236 OCH₂CH₂SMe i-Pr1 CCl₃ 5-237 OCH₂CH₂SMe Me 2 CCl₃ 5-238 OCH₂CH₂SMe Et 2 CCl₃ 5-239OCH₂CH₂SMe n-Pr 2 CCl₃ 5-240 OCH₂CH₂SMe i-Pr 2 CCl₃ 5-241 OCH₂CH₂SO₂MeMe 0 CCl₃ 5-242 OCH₂CH₂SO₂Me Et 0 CCl₃ 5-243 OCH₂CH₂SO₂Me n-Pr 0 CCl₃5-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃ 5-245 OCH₂CH₂SO₂Me Me 1 CCl₃ 5-246OCH₂CH₂SO₂Me Et 1 CCl₃ 5-247 OCH₂CH₂SO₂Me n-Pr 1 CCl₃ 5-248 OCH₂CH₂SO₂Mei-Pr 1 CCl₃ 5-249 OCH₂CH₂SO₂Me Me 2 CCl₃ 5-250 OCH₂CH₂SO₂Me Et 2 CCl₃5-251 OCH₂CH₂SO₂Me n-Pr 2 CCl₃ 5-252 OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 5-253 OMeMe 0 CHF2 5-254 OMe Et 0 CHF2 5-255 OMe n-Pr 0 CHF2 5-256 OMe i-Pr 0CHF2 5-257 OMe Me 1 CHF2 5-258 OMe Et 1 CHF2 5-259 OMe n-Pr 1 CHF2 5-260OMe i-Pr 1 CHF2 5-261 OMe Me 2 CHF2 5-262 OMe Et 2 CHF2 5-263 OMe n-Pr 2CHF2 5-264 OMe i-Pr 2 CHF2 5-265 OEt Me 0 CHF2 5-266 OEt Et 0 CHF2 5-267OEt n-Pr 0 CHF2 5-268 OEt i-Pr 0 CHF2 5-269 OEt Me 1 CHF2 5-270 OEt Et 1CHF2 5-271 OEt n-Pr 1 CHF2 5-272 OEt i-Pr 1 CHF2 5-273 OEt Me 2 CHF25-274 OEt Et 2 CHF2 5-275 OEt n-Pr 2 CHF2 5-276 OEt i-Pr 2 CHF2 5-277O—CH₂—c-Pr Me 0 CHF2 5-278 O—CH₂—c-Pr Et 0 CHF2 5-279 O—CH₂—c-Pr n-Pr 0CHF2 5-280 O—CH₂—c-Pr i-Pr 0 CHF2 5-281 O—CH₂—c-Pr Me 1 CHF2 5-282O—CH₂—c-Pr Et 1 CHF2 5-283 O—CH₂—c-Pr n-Pr 1 CHF2 5-284 O—CH₂—c-Pr i-Pr1 CHF2 5-285 O—CH₂—c-Pr Me 2 CHF2 5-286 O—CH₂—c-Pr Et 2 CHF2 5-287O—CH₂—c-Pr n-Pr 2 CHF2 5-288 O—CH₂—c-Pr i-Pr 2 CHF2 5-289 OCH₂CH₂OMe Me0 CHF2 5-290 OCH₂CH₂OMe Et 0 CHF2 5-291 OCH₂CH₂OMe n-Pr 0 CHF2 5-292OCH₂CH₂OMe i-Pr 0 CHF2 5-293 OCH₂CH₂OMe Me 1 CHF2 5-294 OCH₂CH₂OMe Et 1CHF2 5-295 OCH₂CH₂OMe n-Pr 1 CHF2 5-296 OCH₂CH₂OMe i-Pr 1 CHF2 5-297OCH₂CH₂OMe Me 2 CHF2 5-298 OCH₂CH₂OMe Et 2 CHF2 5-299 OCH₂CH₂OMe n-Pr 2CHF2 5-300 OCH₂CH₂OMe i-Pr 2 CHF2 5-301 OCH₂CH₂SMe Me 0 CHF2 5-302OCH₂CH₂SMe Et 0 CHF2 5-303 OCH₂CH₂SMe n-Pr 0 CHF2 5-304 OCH₂CH₂SMe i-Pr0 CHF2 5-305 OCH₂CH₂SMe Me 1 CHF2 5-306 OCH₂CH₂SMe Et 1 CHF2 5-307OCH₂CH₂SMe n-Pr 1 CHF2 5-308 OCH₂CH₂SMe i-Pr 1 CHF2 5-309 OCH₂CH₂SMe Me2 CHF2 5-310 OCH₂CH₂SMe Et 2 CHF2 5-311 OCH₂CH₂SMe n-Pr 2 CHF2 5-312OCH₂CH₂SMe i-Pr 2 CHF2 5-313 OCH₂CH₂SO₂Me Me 0 CHF2 5-314 OCH₂CH₂SO₂MeEt 0 CHF2 5-315 OCH₂CH₂SO₂Me n-Pr 0 CHF2 5-316 OCH₂CH₂SO₂Me i-Pr 0 CHF25-317 OCH₂CH₂SO₂Me Me 1 CHF2 5-318 OCH₂CH₂SO₂Me Et 1 CHF2 5-319OCH₂CH₂SO₂Me n-Pr 1 CHF2 5-320 OCH₂CH₂SO₂Me i-Pr 1 CHF2 5-321OCH₂CH₂SO₂Me Me 2 CHF2 5-322 OCH₂CH₂SO₂Me Et 2 CHF2 5-323 OCH₂CH₂SO₂Men-Pr 2 CHF2 5-324 OCH₂CH₂SO₂Me i-Pr 2 CHF2 5-325 OMe Me 0 CF(CF₃)₂ 5-326OMe Et 0 CF(CF₃)₂ 5-327 OMe n-Pr 0 CF(CF₃)₂ 5-328 OMe i-Pr 0 CF(CF₃)₂5-329 OMe Me 1 CF(CF₃)₂ 5-330 OMe Et 1 CF(CF₃)₂ 5-331 OMe n-Pr 1CF(CF₃)₂ 5-332 OMe i-Pr 1 CF(CF₃)₂ 5-333 OMe Me 2 CF(CF₃)₂ 5-334 OMe Et2 CF(CF₃)₂ 5-335 OMe n-Pr 2 CF(CF₃)₂ 5-336 OMe i-Pr 2 CF(CF₃)₂ 5-337 OEtMe 0 CF(CF₃)₂ 5-338 OEt Et 0 CF(CF₃)₂ 5-339 OEt n-Pr 0 CF(CF₃)₂ 5-340OEt i-Pr 0 CF(CF₃)₂ 5-341 OEt Me 1 CF(CF₃)₂ 5-342 OEt Et 1 CF(CF₃)₂5-343 OEt n-Pr 1 CF(CF₃)₂ 5-344 OEt i-Pr 1 CF(CF₃)₂ 5-345 OEt Me 2CF(CF₃)₂ 5-346 OEt Et 2 CF(CF₃)₂ 5-347 OEt n-Pr 2 CF(CF₃)₂ 5-348 OEti-Pr 2 CF(CF₃)₂ 5-349 O—CH₂—c-Pr Me 0 CF(CF₃)₂ 5-350 O—CH₂—c-Pr Et 0CF(CF₃)₂ 5-351 O—CH₂—c-Pr n-Pr 0 CF(CF₃)₂ 5-352 O—CH₂—c-Pr i-Pr 0CF(CF₃)₂ 5-353 O—CH₂—c-Pr Me 1 CF(CF₃)₂ 5-354 O—CH₂—c-Pr Et 1 CF(CF₃)₂5-355 O—CH₂—c-Pr n-Pr 1 CF(CF₃)₂ 5-356 O—CH₂—c-Pr i-Pr 1 CF(CF₃)₂ 5-357O—CH₂—c-Pr Me 2 CF(CF₃)₂ 5-358 O—CH₂—c-Pr Et 2 CF(CF₃)₂ 5-359 O—CH₂—c-Prn-Pr 2 CF(CF₃)₂ 5-360 O—CH₂—c-Pr i-Pr 2 CF(CF₃)₂ 5-361 OCH₂CH₂OMe Me 0CF(CF₃)₂ 5-362 OCH₂CH₂OMe Et 0 CF(CF₃)₂ 5-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂5-364 OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 5-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 5-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 5-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 5-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 5-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 5-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 5-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 5-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 5-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 5-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 5-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 5-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 5-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 5-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 5-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 5-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 5-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 5-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 5-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 5-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 5-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 5-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 5-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 5-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 5-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 5-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 5-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 5-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 5-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 5-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 5-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 5-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

TABLE 6 Compounds of the formula (I) according to the invention in whichR² is phenylthio and R³ to R⁸ are each hydrogen. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 6-1 OMe Me 0 CF₃ 6-2 OMeEt 0 CF₃ 6-3 OMe n-Pr 0 CF₃ 6-4 OMe i-Pr 0 CF₃ 6-5 OMe Me 1 CF₃ 6-6 OMeEt 1 CF₃ 6-7 OMe n-Pr 1 CF₃ 6-8 OMe i-Pr 1 CF₃ 6-9 OMe Me 2 CF₃ 6-10 OMeEt 2 CF₃ 6-11 OMe n-Pr 2 CF₃ 6-12 OMe i-Pr 2 CF₃ 6-13 OEt Me 0 CF₃ 6-14OEt Et 0 CF₃ 6-15 OEt n-Pr 0 CF₃ 6-16 OEt i-Pr 0 CF₃ 6-17 OEt Me 1 CF₃6-18 OEt Et 1 CF₃ 6-19 OEt n-Pr 1 CF₃ 6-20 OEt i-Pr 1 CF₃ 6-21 OEt Me 2CF₃ 6-22 OEt Et 2 CF₃ 6-23 OEt n-Pr 2 CF₃ 6-24 OEt i-Pr 2 CF₃ 6-25OCH₂CH₂OMe Me 0 CF₃ 6-26 OCH₂CH₂OMe Et 0 CF₃ 6-27 OCH₂CH₂OMe n-Pr 0 CF₃6-28 OCH₂CH₂OMe i-Pr 0 CF₃ 6-29 OCH₂CH₂OMe Me 1 CF₃ 6-30 OCH₂CH₂OMe Et 1CF₃ 6-31 OCH₂CH₂OMe n-Pr 1 CF₃ 6-32 OCH₂CH₂OMe i-Pr 1 CF₃ 6-33OCH₂CH₂OMe Me 2 CF₃ 6-34 OCH₂CH₂OMe Et 2 CF₃ 6-35 OCH₂CH₂OMe n-Pr 2 CF₃6-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 7 Compounds of the formula (I) according to the invention in whichR² is phenylthio, R³ and R⁴ are each methyl and R⁵ to R⁸ are eachhydrogen. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 7-1 OMe Me 0 CF₃ 7-2 OMeEt 0 CF₃ 7-3 OMe n-Pr 0 CF₃ 7-4 OMe i-Pr 0 CF₃ 7-5 OMe Me 1 CF₃ 7-6 OMeEt 1 CF₃ 7-7 OMe n-Pr 1 CF₃ 7-8 OMe i-Pr 1 CF₃ 7-9 OMe Me 2 CF₃ 7-10 OMeEt 2 CF₃ 7-11 OMe n-Pr 2 CF₃ 7-12 OMe i-Pr 2 CF₃ 7-13 OEt Me 0 CF₃ 7-14OEt Et 0 CF₃ 7-15 OEt n-Pr 0 CF₃ 7-16 OEt i-Pr 0 CF₃ 7-17 OEt Me 1 CF₃7-18 OEt Et 1 CF₃ 7-19 OEt n-Pr 1 CF₃ 7-20 OEt i-Pr 1 CF₃ 7-21 OEt Me 2CF₃ 7-22 OEt Et 2 CF₃ 7-23 OEt n-Pr 2 CF₃ 7-24 OEt i-Pr 2 CF₃ 7-25OCH₂CH₂OMe Me 0 CF₃ 7-26 OCH₂CH₂OMe Et 0 CF₃ 7-27 OCH₂CH₂OMe n-Pr 0 CF₃7-28 OCH₂CH₂OMe i-Pr 0 CF₃ 7-29 OCH₂CH₂OMe Me 1 CF₃ 7-30 OCH₂CH₂OMe Et 1CF₃ 7-31 OCH₂CH₂OMe n-Pr 1 CF₃ 7-32 OCH₂CH₂OMe i-Pr 1 CF₃ 7-33OCH₂CH₂OMe Me 2 CF₃ 7-34 OCH₂CH₂OMe Et 2 CF₃ 7-35 OCH₂CH₂OMe n-Pr 2 CF₃7-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 8 Compounds of the formula (I) according to the invention in whichR² is phenylthio, R³, R⁴, R⁷ and R⁸ are each hydrogen and R⁵ and R⁶ areeach methyl. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 8-1 OMe Me 0 CF₃ 8-2 OMeEt 0 CF₃ 8-3 OMe n-Pr 0 CF₃ 8-4 OMe i-Pr 0 CF₃ 8-5 OMe Me 1 CF₃ 8-6 OMeEt 1 CF₃ 8-7 OMe n-Pr 1 CF₃ 8-8 OMe i-Pr 1 CF₃ 8-9 OMe Me 2 CF₃ 8-10 OMeEt 2 CF₃ 8-11 OMe n-Pr 2 CF₃ 8-12 OMe i-Pr 2 CF₃ 8-13 OEt Me 0 CF₃ 8-14OEt Et 0 CF₃ 8-15 OEt n-Pr 0 CF₃ 8-16 OEt i-Pr 0 CF₃ 8-17 OEt Me 1 CF₃8-18 OEt Et 1 CF₃ 8-19 OEt n-Pr 1 CF₃ 8-20 OEt i-Pr 1 CF₃ 8-21 OEt Me 2CF₃ 8-22 OEt Et 2 CF₃ 8-23 OEt n-Pr 2 CF₃ 8-24 OEt i-Pr 2 CF₃ 8-25OCH₂CH₂OMe Me 0 CF₃ 8-26 OCH₂CH₂OMe Et 0 CF₃ 8-27 OCH₂CH₂OMe n-Pr 0 CF₃8-28 OCH₂CH₂OMe i-Pr 0 CF₃ 8-29 OCH₂CH₂OMe Me 1 CF₃ 8-30 OCH₂CH₂OMe Et 1CF₃ 8-31 OCH₂CH₂OMe n-Pr 1 CF₃ 8-32 OCH₂CH₂OMe i-Pr 1 CF₃ 8-33OCH₂CH₂OMe Me 2 CF₃ 8-34 OCH₂CH₂OMe Et 2 CF₃ 8-35 OCH₂CH₂OMe n-Pr 2 CF₃8-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 9 Compounds of the formula (I) according to the invention in whichR² is phenylthio, R³ to R⁶ are each hydrogen and R⁷ and R⁸ are eachmethyl. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 9-1 OMe Me 0 CF₃ 9-2 OMeEt 0 CF₃ 9-3 OMe n-Pr 0 CF₃ 9-4 OMe i-Pr 0 CF₃ 9-5 OMe Me 1 CF₃ 9-6 OMeEt 1 CF₃ 9-7 OMe n-Pr 1 CF₃ 9-8 OMe i-Pr 1 CF₃ 9-9 OMe Me 2 CF₃ 9-10 OMeEt 2 CF₃ 9-11 OMe n-Pr 2 CF₃ 9-12 OMe i-Pr 2 CF₃ 9-13 OEt Me 0 CF₃ 9-14OEt Et 0 CF₃ 9-15 OEt n-Pr 0 CF₃ 9-16 OEt i-Pr 0 CF₃ 9-17 OEt Me 1 CF₃9-18 OEt Et 1 CF₃ 9-19 OEt n-Pr 1 CF₃ 9-20 OEt i-Pr 1 CF₃ 9-21 OEt Me 2CF₃ 9-22 OEt Et 2 CF₃ 9-23 OEt n-Pr 2 CF₃ 9-24 OEt i-Pr 2 CF₃ 9-25OCH₂CH₂OMe Me 0 CF₃ 9-26 OCH₂CH₂OMe Et 0 CF₃ 9-27 OCH₂CH₂OMe n-Pr 0 CF₃9-28 OCH₂CH₂OMe i-Pr 0 CF₃ 9-29 OCH₂CH₂OMe Me 1 CF₃ 9-30 OCH₂CH₂OMe Et 1CF₃ 9-31 OCH₂CH₂OMe n-Pr 1 CF₃ 9-32 OCH₂CH₂OMe i-Pr 1 CF₃ 9-33OCH₂CH₂OMe Me 2 CF₃ 9-34 OCH₂CH₂OMe Et 2 CF₃ 9-35 OCH₂CH₂OMe n-Pr 2 CF₃9-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 10 Compounds of the formula (I) according to the invention inwhich R² is phenylthio, R³, R⁴, R⁵, R⁷ and R⁸ are each hydrogen and R⁶is methyl. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 10-1 OMe Me 0 CF₃ 10-2 OMeEt 0 CF₃ 10-3 OMe n-Pr 0 CF₃ 10-4 OMe i-Pr 0 CF₃ 10-5 OMe Me 1 CF₃ 10-6OMe Et 1 CF₃ 10-7 OMe n-Pr 1 CF₃ 10-8 OMe i-Pr 1 CF₃ 10-9 OMe Me 2 CF₃10-10 OMe Et 2 CF₃ 10-11 OMe n-Pr 2 CF₃ 10-12 OMe i-Pr 2 CF₃ 10-13 OEtMe 0 CF₃ 10-14 OEt Et 0 CF₃ 10-15 OEt n-Pr 0 CF₃ 10-16 OEt i-Pr 0 CF₃10-17 OEt Me 1 CF₃ 10-18 OEt Et 1 CF₃ 10-19 OEt n-Pr 1 CF₃ 10-20 OEti-Pr 1 CF₃ 10-21 OEt Me 2 CF₃ 10-22 OEt Et 2 CF₃ 10-23 OEt n-Pr 2 CF₃10-24 OEt i-Pr 2 CF₃ 10-25 OCH₂CH₂OMe Me 0 CF₃ 10-26 OCH₂CH₂OMe Et 0 CF₃10-27 OCH₂CH₂OMe n-Pr 0 CF₃ 10-28 OCH₂CH₂OMe i-Pr 0 CF₃ 10-29 OCH₂CH₂OMeMe 1 CF₃ 10-30 OCH₂CH₂OMe Et 1 CF₃ 10-31 OCH₂CH₂OMe n-Pr 1 CF₃ 10-32OCH₂CH₂OMe i-Pr 1 CF₃ 10-33 OCH₂CH₂OMe Me 2 CF₃ 10-34 OCH₂CH₂OMe Et 2CF₃ 10-35 OCH₂CH₂OMe n-Pr 2 CF₃ 10-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 11 Compounds of the formula (I) according to the invention inwhich R² is phenylthio, R⁴, R⁵, R⁶ and R⁷ are each hydrogen and R³ andR⁸ together are an ethylene group. (I)

Physical data: No. X R¹ n Y ¹H-NMR: δ [CDCl₃] 11-1 OMe Me 0 CF₃ 11-2 OMeEt 0 CF₃ 11-3 OMe n-Pr 0 CF₃ 11-4 OMe i-Pr 0 CF₃ 11-5 OMe Me 1 CF₃ 11-6OMe Et 1 CF₃ 11-7 OMe n-Pr 1 CF₃ 11-8 OMe i-Pr 1 CF₃ 11-9 OMe Me 2 CF₃11-10 OMe Et 2 CF₃ 11-11 OMe n-Pr 2 CF₃ 11-12 OMe i-Pr 2 CF₃ 11-13 OEtMe 0 CF₃ 11-14 OEt Et 0 CF₃ 11-15 OEt n-Pr 0 CF₃ 11-16 OEt i-Pr 0 CF₃11-17 OEt Me 1 CF₃ 11-18 OEt Et 1 CF₃ 11-19 OEt n-Pr 1 CF₃ 11-20 OEti-Pr 1 CF₃ 11-21 OEt Me 2 CF₃ 11-22 OEt Et 2 CF₃ 11-23 OEt n-Pr 2 CF₃11-24 OEt i-Pr 2 CF₃ 11-25 OCH₂CH₂OMe Me 0 CF₃ 11-26 OCH₂CH₂OMe Et 0 CF₃11-27 OCH₂CH₂OMe n-Pr 0 CF₃ 11-28 OCH₂CH₂OMe i-Pr 0 CF₃ 11-29 OCH₂CH₂OMeMe 1 CF₃ 11-30 OCH₂CH₂OMe Et 1 CF₃ 11-31 OCH₂CH₂OMe n-Pr 1 CF₃ 11-32OCH₂CH₂OMe i-Pr 1 CF₃ 11-33 OCH₂CH₂OMe Me 2 CF₃ 11-34 OCH₂CH₂OMe Et 2CF₃ 11-35 OCH₂CH₂OMe n-Pr 2 CF₃ 11-36 OCH₂CH₂OMe i-Pr 2 CF₃

TABLE 12 Compounds of the formula (II) according to the invention (II)

Physical data: ¹H-NMR: No. X R¹ n Y δ [DMSO-d₆] 12-1 OH Me 0 CF₃ 12-2 OHEt 0 CF₃ 12-3 OH n-Pr 0 CF₃ 12-4 OH i-Pr 0 CF₃ 12-5 OH Me 1 CF₃ 12-6 OHEt 1 CF₃ 12-7 OH n-Pr 1 CF₃ 12-8 OH i-Pr 1 CF₃ 12-9 OH Me 2 CF₃ 12-10 OHEt 2 CF₃ 12-11 OH n-Pr 2 CF₃ 12-12 OH i-Pr 2 CF₃ 12-13 OMe Me 0 CF₃ 7.76(d, 1H), 7.58 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H) 12-14 OMe Et 0 CF₃7.78 (d, 1H), 7.61 (d, 1H), 3.90 (s, 3H), 2.95 (q, 2H), 1.07 (t, 3H)12-15 OMe n-Pr 0 CF₃ 12-16 OMe i-Pr 0 CF₃ 12-17 OMe Me 1 CF₃ 12-18 OMeEt 1 CF₃ 12-19 OMe n-Pr 1 CF₃ 12-20 OMe i-Pr 1 CF₃ 12-21 OMe Me 2 CF₃12-22 OMe Et 2 CF₃ 12-23 OMe n-Pr 2 CF₃ 12-24 OMe i-Pr 2 CF₃ 12-25 OEtMe 0 CF₃ 7.78 (d, 1H), 7.60 (d, 1H), 4.12 (q, 2H), 2.43 (s, 3H), 1.37(t, 3H) 12-26 OEt Et 0 CF₃ 7.78 (d, 1H), 7.61 (d, 1H), 4.12 (q, 2H),2.98 (q, 2H), 1.36 (t, 3H), 1.08 (t, 3H) 12-27 OEt n-Pr 0 CF₃ 12-28 OEti-Pr 0 CF₃ 12-29 OEt Me 1 CF₃ 12-30 OEt Et 1 CF₃ 12-31 OEt n-Pr 1 CF₃12-32 OEt i-Pr 1 CF₃ 12-33 OEt Me 2 CF₃ 12-34 OEt Et 2 CF₃ 12-35 OEtn-Pr 2 CF₃ 12-36 OEt i-Pr 2 CF₃ 12-37 O—CH₂—c-Pr Me 0 CF₃ 7.77 (d, 1H),7.60 (d, 1H), 3.92 (d, 2H), 2.46 (s, 3H), 1.27 (m, 1H), 0.57 (m, 2H),0.33 (m, 2H) 12-38 O—CH₂—c-Pr Et 0 CF₃ 12-39 O—CH₂—c-Pr n-Pr 0 CF₃ 12-40O—CH₂—c-Pr i-Pr 0 CF₃ 12-41 O—CH₂—c-Pr Me 1 CF₃ 12-42 O—CH₂—c-Pr Et 1CF₃ 12-43 O—CH₂—c-Pr n-Pr 1 CF₃ 12-44 O—CH₂—c-Pr i-Pr 1 CF₃ 12-45O—CH₂—c-Pr Me 2 CF₃ 12-46 O—CH₂—c-Pr Et 2 CF₃ 12-47 O—CH₂—c-Pr n-Pr 2CF₃ 12-48 O—CH₂—c-Pr i-Pr 2 CF₃ 12-49 OCH₂CH₂OMe Me 0 CF₃ 7.77 (d, 1H),7.60 (d, 1H), 4.22 (t, 2H), 3.71 (t, 2H), 2.44 (s, 3H) 12-50 OCH₂CH₂OMeEt 0 CF₃ 12-51 OCH₂CH₂OMe n-Pr 0 CF₃ 12-52 OCH₂CH₂OMe i-Pr 0 CF₃ 12-53OCH₂CH₂OMe Me 1 CF₃ 12-54 OCH₂CH₂OMe Et 1 CF₃ 12-55 OCH₂CH₂OMe n-Pr 1CF₃ 12-56 OCH₂CH₂OMe i-Pr 1 CF₃ 12-57 OCH₂CH₂OMe Me 2 CF₃ 12-58OCH₂CH₂OMe Et 2 CF₃ 12-59 OCH₂CH₂OMe n-Pr 2 CF₃ 12-60 OCH₂CH₂OMe i-Pr 2CF₃ 12-61 OCH₂CH₂SMe Me 0 CF₃ 12-62 OCH₂CH₂SMe Et 0 CF₃ 12-63 OCH₂CH₂SMen-Pr 0 CF₃ 12-64 OCH₂CH₂SMe i-Pr 0 CF₃ 12-65 OCH₂CH₂SMe Me 1 CF₃ 12-66OCH₂CH₂SMe Et 1 CF₃ 12-67 OCH₂CH₂SMe n-Pr 1 CF₃ 12-68 OCH₂CH₂SMe i-Pr 1CF₃ 12-69 OCH₂CH₂SMe Me 2 CF₃ 12-70 OCH₂CH₂SMe Et 2 CF₃ 12-71 OCH₂CH₂SMen-Pr 2 CF₃ 12-72 OCH₂CH₂SMe i-Pr 2 CF₃ 12-73 OCH₂CH₂SO₂Me Me 0 CF₃ 12-74OCH₂CH₂SO₂Me Et 0 CF₃ 12-75 OCH₂CH₂SO₂Me n-Pr 0 CF₃ 12-76 OCH₂CH₂SO₂Mei-Pr 0 CF₃ 12-77 OCH₂CH₂SO₂Me Me 1 CF₃ 12-78 OCH₂CH₂SO₂Me Et 1 CF₃ 12-79OCH₂CH₂SO₂Me n-Pr 1 CF₃ 12-80 OCH₂CH₂SO₂Me i-Pr 1 CF₃ 12-81 OCH₂CH₂SO₂MeMe 2 CF₃ 12-82 OCH₂CH₂SO₂Me Et 2 CF₃ 12-83 OCH₂CH₂SO₂Me n-Pr 2 CF₃ 12-84OCH₂CH₂SO₂Me i-Pr 2 CF₃ 12-85 OCOMe Me 0 CF₃ 12-86 OCOMe Et 0 CF₃ 12-87OCOMe n-Pr 0 CF₃ 12-88 OCOMe i-Pr 0 CF₃ 12-89 OCOMe Me 1 CF₃ 12-90 OCOMeEt 1 CF₃ 12-91 OCOMe n-Pr 1 CF₃ 12-92 OCOMe i-Pr 1 CF₃ 12-93 OCOMe Me 2CF₃ 12-94 OCOMe Et 2 CF₃ 12-95 OCOMe n-Pr 2 CF₃ 12-96 OCOMe i-Pr 2 CF₃12-97 OSO₂Me Me 0 CF₃ 12-98 OSO₂Me Et 0 CF₃ 12-99 OSO₂Me n-Pr 0 CF₃12-100 OSO₂Me i-Pr 0 CF₃ 12-101 OSO₂Me Me 1 CF₃ 12-102 OSO₂Me Et 1 CF₃12-103 OSO₂Me n-Pr 1 CF₃ 12-104 OSO₂Me i-Pr 1 CF₃ 12-105 OSO₂Me Me 2 CF₃12-106 OSO₂Me Et 2 CF₃ 12-107 OSO₂Me n-Pr 2 CF₃ 12-108 OSO₂Me i-Pr 2 CF₃12-109 OMe Me 0 C₂F₅ 12-110 OMe Et 0 C₂F₅ 12-111 OMe n-Pr 0 C₂F₅ 12-112OMe i-Pr 0 C₂F₅ 12-113 OMe Me 1 C₂F₅ 12-114 OMe Et 1 C₂F₅ 12-115 OMen-Pr 1 C₂F₅ 12-116 OMe i-Pr 1 C₂F₅ 12-117 OMe Me 2 C₂F₅ 12-118 OMe Et 2C₂F₅ 12-119 OMe n-Pr 2 C₂F₅ 12-120 OMe i-Pr 2 C₂F₅ 12-121 OEt Me 0 C₂F₅12-122 OEt Et 0 C₂F₅ 12-123 OEt n-Pr 0 C₂F₅ 12-124 OEt i-Pr 0 C₂F₅12-125 OEt Me 1 C₂F₅ 12-126 OEt Et 1 C₂F₅ 12-127 OEt n-Pr 1 C₂F₅ 12-128OEt i-Pr 1 C₂F₅ 12-129 OEt Me 2 C₂F₅ 12-130 OEt Et 2 C₂F₅ 12-131 OEtn-Pr 2 C₂F₅ 12-132 OEt i-Pr 2 C₂F₅ 12-133 O—CH₂—c-Pr Me 0 C₂F₅ 12-134O—CH₂—c-Pr Et 0 C₂F₅ 12-135 O—CH₂—c-Pr n-Pr 0 C₂F₅ 12-136 O—CH₂—c-Pri-Pr 0 C₂F₅ 12-137 O—CH₂—c-Pr Me 1 C₂F₅ 12-138 O—CH₂—c-Pr Et 1 C₂F₅12-139 O—CH₂—c-Pr n-Pr 1 C₂F₅ 12-140 O—CH₂—c-Pr i-Pr 1 C₂F₅ 12-141O—CH₂—c-Pr Me 2 C₂F₅ 12-142 O—CH₂—c-Pr Et 2 C₂F₅ 12-143 O—CH₂—c-Pr n-Pr2 C₂F₅ 12-144 O—CH₂—c-Pr i-Pr 2 C₂F₅ 12-145 OCH₂CH₂OMe Me 0 C₂F₅ 12-146OCH₂CH₂OMe Et 0 C₂F₅ 12-147 OCH₂CH₂OMe n-Pr 0 C₂F₅ 12-148 OCH₂CH₂OMei-Pr 0 C₂F₅ 12-149 OCH₂CH₂OMe Me 1 C₂F₅ 12-150 OCH₂CH₂OMe Et 1 C₂F₅12-151 OCH₂CH₂OMe n-Pr 1 C₂F₅ 12-152 OCH₂CH₂OMe i-Pr 1 C₂F₅ 12-153OCH₂CH₂OMe Me 2 C₂F₅ 12-154 OCH₂CH₂OMe Et 2 C₂F₅ 12-155 OCH₂CH₂OMe n-Pr2 C₂F₅ 12-156 OCH₂CH₂OMe i-Pr 2 C₂F₅ 12-157 OCH₂CH₂SMe Me 0 C₂F₅ 12-158OCH₂CH₂SMe Et 0 C₂F₅ 12-159 OCH₂CH₂SMe n-Pr 0 C₂F₅ 12-160 OCH₂CH₂SMei-Pr 0 C₂F₅ 12-161 OCH₂CH₂SMe Me 1 C₂F₅ 12-162 OCH₂CH₂SMe Et 1 C₂F₅12-163 OCH₂CH₂SMe n-Pr 1 C₂F₅ 12-164 OCH₂CH₂SMe i-Pr 1 C₂F₅ 12-165OCH₂CH₂SMe Me 2 C₂F₅ 12-166 OCH₂CH₂SMe Et 2 C₂F₅ 12-167 OCH₂CH₂SMe n-Pr2 C₂F₅ 12-168 OCH₂CH₂SMe i-Pr 2 C₂F₅ 12-169 OCH₂CH₂SO₂Me Me 0 C₂F₅12-170 OCH₂CH₂SO₂Me Et 0 C₂F₅ 12-171 OCH₂CH₂SO₂Me n-Pr 0 C₂F₅ 12-172OCH₂CH₂SO₂Me i-Pr 0 C₂F₅ 12-173 OCH₂CH₂SO₂Me Me 1 C₂F₅ 12-174OCH₂CH₂SO₂Me Et 1 C₂F₅ 12-175 OCH₂CH₂SO₂Me n-Pr 1 C₂F₅ 12-176OCH₂CH₂SO₂Me i-Pr 1 C₂F₅ 12-177 OCH₂CH₂SO₂Me Me 2 C₂F₅ 12-178OCH₂CH₂SO₂Me Et 2 C₂F₅ 12-179 OCH₂CH₂SO₂Me n-Pr 2 C₂F₅ 12-180OCH₂CH₂SO₂Me i-Pr 2 C₂F₅ 12-181 OMe Me 0 CCl₃ 12-182 OMe Et 0 CCl₃12-183 OMe n-Pr 0 CCl₃ 12-184 OMe i-Pr 0 CCl₃ 12-185 OMe Me 1 CCl₃12-186 OMe Et 1 CCl₃ 12-187 OMe n-Pr 1 CCl₃ 12-188 OMe i-Pr 1 CCl₃12-189 OMe Me 2 CCl₃ 12-190 OMe Et 2 CCl₃ 12-191 OMe n-Pr 2 CCl₃ 12-192OMe i-Pr 2 CCl₃ 12-193 OEt Me 0 CCl₃ 12-194 OEt Et 0 CCl₃ 12-195 OEtn-Pr 0 CCl₃ 12-196 OEt i-Pr 0 CCl₃ 12-197 OEt Me 1 CCl₃ 12-198 OEt Et 1CCl₃ 12-199 OEt n-Pr 1 CCl₃ 12-200 OEt i-Pr 1 CCl₃ 12-201 OEt Me 2 CCl₃12-202 OEt Et 2 CCl₃ 12-203 OEt n-Pr 2 CCl₃ 12-204 OEt i-Pr 2 CCl₃12-205 O—CH₂—c-Pr Me 0 CCl₃ 12-206 O—CH₂—c-Pr Et 0 CCl₃ 12-207O—CH₂—c-Pr n-Pr 0 CCl₃ 12-208 O—CH₂—c-Pr i-Pr 0 CCl₃ 12-209 O—CH₂—c-PrMe 1 CCl₃ 12-210 O—CH₂—c-Pr Et 1 CCl₃ 12-211 O—CH₂—c-Pr n-Pr 1 CCl₃12-212 O—CH₂—c-Pr i-Pr 1 CCl₃ 12-213 O—CH₂—c-Pr Me 2 CCl₃ 12-214O—CH₂—c-Pr Et 2 CCl₃ 12-215 O—CH₂—c-Pr n-Pr 2 CCl₃ 12-216 O—CH₂—c-Pri-Pr 2 CCl₃ 12-217 OCH₂CH₂OMe Me 0 CCl₃ 12-218 OCH₂CH₂OMe Et 0 CCl₃12-219 OCH₂CH₂OMe n-Pr 0 CCl₃ 12-220 OCH₂CH₂OMe i-Pr 0 CCl₃ 12-221OCH₂CH₂OMe Me 1 CCl₃ 12-222 OCH₂CH₂OMe Et 1 CCl₃ 12-223 OCH₂CH₂OMe n-Pr1 CCl₃ 12-224 OCH₂CH₂OMe i-Pr 1 CCl₃ 12-225 OCH₂CH₂OMe Me 2 CCl₃ 12-226OCH₂CH₂OMe Et 2 CCl₃ 12-227 OCH₂CH₂OMe n-Pr 2 CCl₃ 12-228 OCH₂CH₂OMei-Pr 2 CCl₃ 12-229 OCH₂CH₂SMe Me 0 CCl₃ 12-230 OCH₂CH₂SMe Et 0 CCl₃12-231 OCH₂CH₂SMe n-Pr 0 CCl₃ 12-232 OCH₂CH₂SMe i-Pr 0 CCl₃ 12-233OCH₂CH₂SMe Me 1 CCl₃ 12-234 OCH₂CH₂SMe Et 1 CCl₃ 12-235 OCH₂CH₂SMe n-Pr1 CCl₃ 12-236 OCH₂CH₂SMe i-Pr 1 CCl₃ 12-237 OCH₂CH₂SMe Me 2 CCl₃ 12-238OCH₂CH₂SMe Et 2 CCl₃ 12-239 OCH₂CH₂SMe n-Pr 2 CCl₃ 12-240 OCH₂CH₂SMei-Pr 2 CCl₃ 12-241 OCH₂CH₂SO₂Me Me 0 CCl₃ 12-242 OCH₂CH₂SO₂Me Et 0 CCl₃12-243 OCH₂CH₂SO₂Me n-Pr 0 CCl₃ 12-244 OCH₂CH₂SO₂Me i-Pr 0 CCl₃ 12-245OCH₂CH₂SO₂Me Me 1 CCl₃ 12-246 OCH₂CH₂SO₂Me Et 1 CCl₃ 12-247 OCH₂CH₂SO₂Men-Pr 1 CCl₃ 12-248 OCH₂CH₂SO₂Me i-Pr 1 CCl₃ 12-249 OCH₂CH₂SO₂Me Me 2CCl₃ 12-250 OCH₂CH₂SO₂Me Et 2 CCl₃ 12-251 OCH₂CH₂SO₂Me n-Pr 2 CCl₃12-252 OCH₂CH₂SO₂Me i-Pr 2 CCl₃ 12-253 OMe Me 0 CHF2 12-254 OMe Et 0CHF2 12-255 OMe n-Pr 0 CHF2 12-256 OMe i-Pr 0 CHF2 12-257 OMe Me 1 CHF212-258 OMe Et 1 CHF2 12-259 OMe n-Pr 1 CHF2 12-260 OMe i-Pr 1 CHF212-261 OMe Me 2 CHF2 12-262 OMe Et 2 CHF2 12-263 OMe n-Pr 2 CHF2 12-264OMe i-Pr 2 CHF2 12-265 OEt Me 0 CHF2 12-266 OEt Et 0 CHF2 12-267 OEtn-Pr 0 CHF2 12-268 OEt i-Pr 0 CHF2 12-269 OEt Me 1 CHF2 12-270 OEt Et 1CHF2 12-271 OEt n-Pr 1 CHF2 12-272 OEt i-Pr 1 CHF2 12-273 OEt Me 2 CHF212-274 OEt Et 2 CHF2 12-275 OEt n-Pr 2 CHF2 12-276 OEt i-Pr 2 CHF212-277 O—CH₂—c-Pr Me 0 CHF2 12-278 O—CH₂—c-Pr Et 0 CHF2 12-279O—CH₂—c-Pr n-Pr 0 CHF2 12-280 O—CH₂—c-Pr i-Pr 0 CHF2 12-281 O—CH₂—c-PrMe 1 CHF2 12-282 O—CH₂—c-Pr Et 1 CHF2 12-283 O—CH₂—c-Pr n-Pr 1 CHF212-284 O—CH₂—c-Pr i-Pr 1 CHF2 12-285 O—CH₂—c-Pr Me 2 CHF2 12-286O—CH₂—c-Pr Et 2 CHF2 12-287 O—CH₂—c-Pr n-Pr 2 CHF2 12-288 O—CH₂—c-Pri-Pr 2 CHF2 12-289 OCH₂CH₂OMe Me 0 CHF2 12-290 OCH₂CH₂OMe Et 0 CHF212-291 OCH₂CH₂OMe n-Pr 0 CHF2 12-292 OCH₂CH₂OMe i-Pr 0 CHF2 12-293OCH₂CH₂OMe Me 1 CHF2 12-294 OCH₂CH₂OMe Et 1 CHF2 12-295 OCH₂CH₂OMe n-Pr1 CHF2 12-296 OCH₂CH₂OMe i-Pr 1 CHF2 12-297 OCH₂CH₂OMe Me 2 CHF2 12-298OCH₂CH₂OMe Et 2 CHF2 12-299 OCH₂CH₂OMe n-Pr 2 CHF2 12-300 OCH₂CH₂OMei-Pr 2 CHF2 12-301 OCH₂CH₂SMe Me 0 CHF2 12-302 OCH₂CH₂SMe Et 0 CHF212-303 OCH₂CH₂SMe n-Pr 0 CHF2 12-304 OCH₂CH₂SMe i-Pr 0 CHF2 12-305OCH₂CH₂SMe Me 1 CHF2 12-306 OCH₂CH₂SMe Et 1 CHF2 12-307 OCH₂CH₂SMe n-Pr1 CHF2 12-308 OCH₂CH₂SMe i-Pr 1 CHF2 12-309 OCH₂CH₂SMe Me 2 CHF2 12-310OCH₂CH₂SMe Et 2 CHF2 12-311 OCH₂CH₂SMe n-Pr 2 CHF2 12-312 OCH₂CH₂SMei-Pr 2 CHF2 12-313 OCH₂CH₂SO₂Me Me 0 CHF2 12-314 OCH₂CH₂SO₂Me Et 0 CHF212-315 OCH₂CH₂SO₂Me n-Pr 0 CHF2 12-316 OCH₂CH₂SO₂Me i-Pr 0 CHF2 12-317OCH₂CH₂SO₂Me Me 1 CHF2 12-318 OCH₂CH₂SO₂Me Et 1 CHF2 12-319 OCH₂CH₂SO₂Men-Pr 1 CHF2 12-320 OCH₂CH₂SO₂Me i-Pr 1 CHF2 12-321 OCH₂CH₂SO₂Me Me 2CHF2 12-322 OCH₂CH₂SO₂Me Et 2 CHF2 12-323 OCH₂CH₂SO₂Me n-Pr 2 CHF212-324 OCH₂CH₂SO₂Me i-Pr 2 CHF2 12-325 OMe Me 0 CF(CF₃)₂ 12-326 OMe Et 0CF(CF₃)₂ 12-327 OMe n-Pr 0 CF(CF₃)₂ 12-328 OMe i-Pr 0 CF(CF₃)₂ 12-329OMe Me 1 CF(CF₃)₂ 12-330 OMe Et 1 CF(CF₃)₂ 12-331 OMe n-Pr 1 CF(CF₃)₂12-332 OMe i-Pr 1 CF(CF₃)₂ 12-333 OMe Me 2 CF(CF₃)₂ 12-334 OMe Et 2CF(CF₃)₂ 12-335 OMe n-Pr 2 CF(CF₃)₂ 12-336 OMe i-Pr 2 CF(CF₃)₂ 12-337OEt Me 0 CF(CF₃)₂ 12-338 OEt Et 0 CF(CF₃)₂ 12-339 OEt n-Pr 0 CF(CF₃)₂12-340 OEt i-Pr 0 CF(CF₃)₂ 12-341 OEt Me 1 CF(CF₃)₂ 12-342 OEt Et 1CF(CF₃)₂ 12-343 OEt n-Pr 1 CF(CF₃)₂ 12-344 OEt i-Pr 1 CF(CF₃)₂ 12-345OEt Me 2 CF(CF₃)₂ 12-346 OEt Et 2 CF(CF₃)₂ 12-347 OEt n-Pr 2 CF(CF₃)₂12-348 OEt i-Pr 2 CF(CF₃)₂ 12-349 O—CH₂—c-Pr Me 0 CF(CF₃)₂ 12-350O—CH₂—c-Pr Et 0 CF(CF₃)₂ 12-351 O—CH₂—c-Pr n-Pr 0 CF(CF₃)₂ 12-352O—CH₂—c-Pr i-Pr 0 CF(CF₃)₂ 12-353 O—CH₂—c-Pr Me 1 CF(CF₃)₂ 12-354O—CH₂—c-Pr Et 1 CF(CF₃)₂ 12-355 O—CH₂—c-Pr n-Pr 1 CF(CF₃)₂ 12-356O—CH₂—c-Pr i-Pr 1 CF(CF₃)₂ 12-357 O—CH₂—c-Pr Me 2 CF(CF₃)₂ 12-358O—CH₂—c-Pr Et 2 CF(CF₃)₂ 12-359 O—CH₂—c-Pr n-Pr 2 CF(CF₃)₂ 12-360O—CH₂—c-Pr i-Pr 2 CF(CF₃)₂ 12-361 OCH₂CH₂OMe Me 0 CF(CF₃)₂ 12-362OCH₂CH₂OMe Et 0 CF(CF₃)₂ 12-363 OCH₂CH₂OMe n-Pr 0 CF(CF₃)₂ 12-364OCH₂CH₂OMe i-Pr 0 CF(CF₃)₂ 12-365 OCH₂CH₂OMe Me 1 CF(CF₃)₂ 12-366OCH₂CH₂OMe Et 1 CF(CF₃)₂ 12-367 OCH₂CH₂OMe n-Pr 1 CF(CF₃)₂ 12-368OCH₂CH₂OMe i-Pr 1 CF(CF₃)₂ 12-369 OCH₂CH₂OMe Me 2 CF(CF₃)₂ 12-370OCH₂CH₂OMe Et 2 CF(CF₃)₂ 12-371 OCH₂CH₂OMe n-Pr 2 CF(CF₃)₂ 12-372OCH₂CH₂OMe i-Pr 2 CF(CF₃)₂ 12-373 OCH₂CH₂SMe Me 0 CF(CF₃)₂ 12-374OCH₂CH₂SMe Et 0 CF(CF₃)₂ 12-375 OCH₂CH₂SMe n-Pr 0 CF(CF₃)₂ 12-376OCH₂CH₂SMe i-Pr 0 CF(CF₃)₂ 12-377 OCH₂CH₂SMe Me 1 CF(CF₃)₂ 12-378OCH₂CH₂SMe Et 1 CF(CF₃)₂ 12-379 OCH₂CH₂SMe n-Pr 1 CF(CF₃)₂ 12-380OCH₂CH₂SMe i-Pr 1 CF(CF₃)₂ 12-381 OCH₂CH₂SMe Me 2 CF(CF₃)₂ 12-382OCH₂CH₂SMe Et 2 CF(CF₃)₂ 12-383 OCH₂CH₂SMe n-Pr 2 CF(CF₃)₂ 12-384OCH₂CH₂SMe i-Pr 2 CF(CF₃)₂ 12-385 OCH₂CH₂SO₂Me Me 0 CF(CF₃)₂ 12-386OCH₂CH₂SO₂Me Et 0 CF(CF₃)₂ 12-387 OCH₂CH₂SO₂Me n-Pr 0 CF(CF₃)₂ 12-388OCH₂CH₂SO₂Me i-Pr 0 CF(CF₃)₂ 12-389 OCH₂CH₂SO₂Me Me 1 CF(CF₃)₂ 12-390OCH₂CH₂SO₂Me Et 1 CF(CF₃)₂ 12-391 OCH₂CH₂SO₂Me n-Pr 1 CF(CF₃)₂ 12-392OCH₂CH₂SO₂Me i-Pr 1 CF(CF₃)₂ 12-393 OCH₂CH₂SO₂Me Me 2 CF(CF₃)₂ 12-394OCH₂CH₂SO₂Me Et 2 CF(CF₃)₂ 12-395 OCH₂CH₂SO₂Me n-Pr 2 CF(CF₃)₂ 12-396OCH₂CH₂SO₂Me i-Pr 2 CF(CF₃)₂

B. FORMULATION EXAMPLES

-   a) A dust is obtained by mixing 10 parts by weight of a compound of    the formula (I) and/or a salt thereof and 90 parts by weight of talc    as inert substance and comminuting the mixture in a hammer mill.-   b) A wettable powder which is readily dispersible in water is    obtained by mixing 25 parts by weight of a compound of the    formula (I) and/or a salt thereof, 64 parts by weight of    kaolin-containing quartz as inert substance, 10 parts by weight of    potassium lignosulfonate and 1 part by weight of sodium    oleoylmethyltaurinate as wetting agent and dispersant, and grinding    the mixture in a pinned-disk mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or a    salt thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example about 255 to above 277° C.) and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or a salt thereof, 75 parts by    weight of cyclohexanone as solvent and 10 parts by weight of    oxethylated nonylphenol as emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I) and/or a        salt thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding the mixture in a pinned-disk mill, and granulating the        powder in a fluidized bed by spraying on water as granulating        liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting, in a colloid mill,    -   25 parts by weight of a compound of the formula (I) and/or a        salt thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurinate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   subsequently grinding the mixture in a bead mill and atomizing        and drying the resulting suspension in a spray tower by means of        a single-substance nozzle.

C. BIOLOGICAL EXAMPLES 1. Pre-Emergence Herbicidal Action AgainstHarmful Plants

Seeds of monocotyledonous or dicotyledonous weed plants or crop plantsare planted in wood-fiber pots in sandy loam and covered with soil. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or emulsion concentrates (EC), are then applied as aqueoussuspension or emulsion at a water application rate of 600 to 800 l/ha(converted) with the addition of 0.2% of wetting agent to the surface ofthe covering soil. After the treatment, the pots are placed in agreenhouse and kept under good growth conditions for the test plants.The visual assessment of the damage to the test plants is carried outafter a trial period of 3 weeks by comparison with untreated controls(herbicidal activity in percent (%): 100% activity=the plants have died,0% activity=like control plants). Here, for example, the compounds Nos.1-21, 5-17 and 5-21 each show, at an application rate of 80 g/ha, anactivity of at least 90% against Abutilon theophrasti and Veronicapersica. The compounds Nos. 2-21 and 2-17 each show, at an applicationrate of 80 g/ha, an activity of at least 90% against Alopecurusmyosuroides, Amaranthus retroflexus and Veronica persica.

2. Post-Emergence Herbicidal Action Against Harmful Plants

Seeds of monocotyledonous and dicotyledonous weed and crop plants areplaced in sandy loam in wood-fiber pots, covered with soil andcultivated in a greenhouse under good growth conditions. 2 to 3 weeksafter sowing, the test plants are treated at the one-leaf stage. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or emulsion concentrates (EC), are then sprayed as aqueoussuspension or emulsion at a water application rate of 600 to 800 l/ha(converted) with the addition of 0.2% of wetting agent onto the greenparts of the plants. After the test plants have been kept in thegreenhouse under optimum growth conditions for about 3 weeks, theactivity of the preparations is rated visually in comparison tountreated controls (herbicidal activity in percent (%): 100%activity=the plants have died, 0% activity=like control plants). Here,for example, the compounds Nos. 3-17, 5-21 and 2-17 each show, at anapplication rate of 80 g/ha, an activity of at least 90% against Avenafatua, Matricaria inodora and Viola tricolor. The compounds Nos. 1-13,1-17, 1-21 and 2-21 each show, at an application rate of 80 g/ha, anactivity of at least 90% against Echinochloa crus galli, Pharbitispurpureum and Stellaria media.

1. A 2-(3-alkylthiobenzoyl)cyclohexanedione of formula (I) and/or a saltthereof

in which R¹ is (C₁-C₆)-alkyl, R² is hydroxyl, SR¹³, or NR¹⁴R¹⁵, R³ andR⁸ independently of one another are hydrogen or (C₁-C₄)-alkyl, or theradicals R³ and R⁸ together form the unit Z which represents an oxygenor sulfur atom or one to four methylene groups, R⁴ and R⁷ independentlyof one another are hydrogen or (C₁-C₄)-alkyl, R⁵ and R⁶ independently ofone another are hydrogen or (C₁-C₄)-alkyl or together with the carbonatom to which they are attached form a carbonyl group, X is OR⁹, OCOR⁹,or OSO₂R¹⁰, R⁹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals selected from the group consisting of halogen,OR¹¹ and S(O)_(m)R¹², R¹⁰ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals selected from the group consisting of halogen,OR¹¹ and S(O)_(m)R¹², R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or(C₂-C₆)-alkynyl, R¹² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or(C₂-C₆)-alkynyl, R¹³ is (C₁-C₄)-alkyl, phenyl which is substituted by sradicals selected from the group consisting of nitro, cyano,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy or (C₁-C₄)-haloalkoxyor is partially or fully halogenated phenyl, R¹⁴ is hydrogen,(C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, R¹⁵ is hydrogen or (C₁-C₄)-alkyl, orR¹⁴ and R¹⁵ together with the nitrogen atom to which they are attachedform a 5- or 6-membered saturated, partially saturated or unsaturatedring, which contains zero, one or two heteroatoms selected from thegroup consisting of oxygen, sulfur and nitrogen, which is substituted bys radicals from the group consisting of cyano, halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, Y is(C₁-C₆)-haloalkyl, m is 0, 1 or 2, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 2.The 2-(3-alkylthiobenzoyl)cyclohexanedione and/or salt as claimed inclaim 1 in which R¹ is methyl, ethyl, n-propyl or isopropyl, R² ishydroxyl, R³ and R⁸ independently of one another are hydrogen or(C₁-C₄)-alkyl, or the radicals R³ and R⁸ together form a methylene orethylene group, R⁴ and R⁷ independently of one another are hydrogen,methyl or ethyl, R⁵ and R⁶ independently of one another are hydrogen,methyl or ethyl, X is OR⁹, OCOR⁹, or OSO₂R¹⁰, R⁹ is cyclopropylmethyl or(C₁-C₆)-alkyl substituted by s methoxy or ethoxy groups, R¹⁰ is(C₁-C₆)-alkyl substituted by s methoxy or ethoxy groups, Y is(C₁-C₃)-haloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or
 3. 3. The2-(3-alkylthiobenzoyl)cyclohexanedione and/or salt as claimed in claim 1in which R¹ is methyl, ethyl, n-propyl or isopropyl, R² is hydroxyl, R³and R⁸ independently of one another are hydrogen, methyl or ethyl, orthe radicals R³ and R⁸ together form a methylene or ethylene group, R⁴and R⁷ independently of one another are hydrogen, methyl or ethyl, R⁵and R⁶ independently of one another are hydrogen, methyl or ethyl, X isOR⁹, R⁹ is cyclopropylmethyl or ethyl or methyl substituted by s methoxyor ethoxy groups, Y is trichloromethyl, difluoromethyl, trifluoromethyl,pentafluoroethyl or heptafluoroisopropyl, n is 0, 1 or 2, s is 0, 1, 2or
 3. 4. A herbicidal composition which comprises a herbicidallyeffective amount of at least one compound as claimed in claim
 1. 5. Theherbicidal composition as claimed in claim 4 comprising a mixture withat least one formulation auxiliary.
 6. A method for controlling unwantedplants which comprises applying an effective amount of at least onecompound as claimed in claim 1 to plants and/or to a site of unwantedvegetation.
 7. A herbicidal composition as claimed in claim 4 forcontrolling unwanted plants.
 8. A composition as claimed in claim 7wherein the compound of formula (I) and/or salt thereof is capable ofcontrolling unwanted plants in crops of useful plants.
 9. A compositionas claimed in claim 8 wherein the useful plants are transgenic usefulplants.
 10. A compound of formula (II) and/or a salt thereof

in which. R¹ is (C₁-C₆)-alkyl, X is OR⁹, OCOR⁹, or OSO₂R¹⁰, R⁹ ishydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals selected from the group consisting of halogen,OR¹¹ and S(O)_(m)R¹², R¹⁰ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl orphenyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals aresubstituted by s radicals selected from the group consisting of halogen,OR¹¹ and S(O)_(m)R¹², R¹¹ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or(C₂-C₆)-alkynyl, R¹² is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or(C₂-C₆)-alkynyl, Y is (C₁-C₆)-haloalkyl, n is 0, 1 or 2, s is 0, 1, 2 or3.